Skip to main content

Nakiterpiosin

  • Chapter
  • First Online:
Total Synthesis of Natural Products

Abstract

For decades, ranchers in central Idaho were puzzled by a mysterious birth defect in their flocks of sheep. A percentage of their lambs, ranging from 1 % to 20 %, were born with only one eye. The Poisonous Plant Research Laboratory of the US Department of Agriculture started to investigate this “malformed lamb disease” in 1954.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. (a) Binns W, James LF, Keeler RF, Balls LD (1968) Cancer Res 28:2323–2326; (b) Keeler RF (1978) Lipids 13:708–715; (c) James LF (1999) J Nat Toxins 8:63–80

    Google Scholar 

  2. (a) Cooper MK, Porter JA, Young KE, Beachy PA (1998) Science 280:1603–1607; (b) Incardona JP, Gaffield W, Kapur RP, Roelink H (1998) Development 125:3553–3562; (c) Chen JK, Taipale J, Cooper MK, Beachy PA (2002) Genes Dev 16:2743–2748

    Google Scholar 

  3. (a) Scalesa SJ, de Sauvage FJ (2009) Trends Pharmacol Sci 30:303–312; (b) Epstein EH (2008) Nat Rev Cancer 8:743–754; (c) van den Brink GR (2007) Physiol Rev 87:1343–1375; (d) Romer J, Curran T (2005) Cancer Res 65:4975–4978; (e) Hooper JE, Scott MP (2005) Nat Rev Mol Cell Biol 6:306–317; (f) Borzillo GV, Lippa B (2005) Curr Top Med Chem 5:147–157; (g) Dellovade T, Romer JT, Curran T, Rubin LL (2006) Annu Rev Neurosci 29:539–563; (h) Yauch RL, Gould SE, Scales SJ, Tang T, Tian H, Ahn CP, Marshall D, Fu L, Januario T, Kallop D, Nannini-Pepe M, Kotkow K, Marsters JC, Rubin LL, de Sauvage FJ (2008) Nature 455:406–410

    Google Scholar 

  4. (a) Smaele ED, Ferretti E, Gulino A (2010) Curr Opin Investig Drugs 11:707–718; (b) Yauch RL, Dijkgraaf GJP, Alicke B, Januario T, Ahn CP, Holcomb T, Pujara K, Stinson J, Callahan CA, Tang T, Bazan JF, Kan Z, Seshagiri S, Hann CL, Gould SE, Low JA, Rudin CM, de Sauvage FJ (2009) Science 326:572–574

    Google Scholar 

  5. (a) Olive KP, Jacobetz MA, Davidson CJ, Gopinathan A, McIntyre D, Honess D, Madhu B, Goldgraben MA, Caldwell ME, Allard D, Frese KK, DeNicola G, Feig C, Combs C, Winter SP, Ireland-Zecchini H, Reichelt S, Howat WJ, Chang A, Dhara M, Wang L, Rückert F, Grützmann R, Pilarsky C, Izeradjene K, Hingorani SR, Huang P, Davies SE, Plunkett W, Egorin M, Hruban RH, Whitebread N, McGovern K, Adams J, Iacobuzio-Donahue C, Griffiths J, Tuveson DA (2009) Science 324:1457–1461; (b) Tremblay MR, Lescarbeau A, Grogan MJ, Tan E, Lin G, Austad BC, Yu L-C, Behnke ML, Nair SJ, Hagel M, White K, Conley J, Manna JD, Alvarez-Diez TM, Hoyt J, Woodward CN, Sydor JR, Pink M, MacDougall J, Campbell MJ, Cushing J, Ferguson J, Curtis MS, McGovern K, Read MA, Palombella VJ, Adams J, Castro AC (2009) J Med Chem 52:4400–4418

    Google Scholar 

  6. Siu LL, Papadopoulos K, Alberts SR, Kirchoff-Ross R, Vakkalagadda B, Lang L, Ahlers CM, Bennett KL, Tornout JMV (2010) J Clin Oncol (Meeting Abstracts) 28(Suppl):2501

    Google Scholar 

  7. (a) Buonamici S, Williams J, Morrissey M, Wang A, Guo R, Vattay A, Hsiao K, Yuan J, Green J, Ospina B, Yu Q, Ostrom L, Fordjour P, Anderson DL, Monahan JE, Kelleher JF, Peukert S, Pan S, Wu X, Maira S-M, García-Echeverría C, Briggs KJ, Watkins DN, Yao Y-M, Lengauer C, Warmuth M, Sellers WR, Dorsch M (2010) Sci Transl Med 2:51ra70; (b) Pan S, Wu X, Jiang J, Gao W, Wan Y, Cheng D, Han D, Liu J, Englund NP, Wang Y, Peukert S, Miller-Moslin K, Yuan J, Guo R, Matsumoto M, Vattay A, Jiang Y, Tsao J, Sun F, Pferdekamper AC, Dodd S, Tuntland T, Maniara W, Kelleher JF III, Yao Y-M, Warmuth M, Williams J, Dorsch M (2010) ACS Med Chem Lett 1:130–134

    Google Scholar 

  8. (a) http://clinicaltrials.gov/; (b) Low JA, de Sauvage FJ (2010) J Clin Oncol. doi:10.1200/JCO.2010.1227.9943; (c) Mahindroo N, Punchihewa C, Fujii N (2009) J Med Chem 52:3829–3845

  9. (a) Teruya T, Nakagawa S, Koyama T, Suenaga K, Kita M, Uemura D (2003) Tetrahedron Lett 44:5171–5173; (b) Teruya T, Nakagawa S, Koyama T, Arimoto H, Kita M, Uemura D (2004) Tetrahedron 60:6989–6993

    Google Scholar 

  10. (a) Plucer-Rosario G (1987) Coral Reefs 5:197–200; (b) Rützler K, Smith KP (1993) Sci Mar 57:381–393; (c) Rützler K, Smith KP (1993) Sci Mar 57:395–403; (d) Liao M-H, Tang S-L, Hsu C-M, Wen K-C, Wu H, Chen W-M, Wang J-T, Meng P-J, Twan W-H, Lu C-K, Dai C-F, Soong K, Chen C-A (2007) Zool Stud 46:520; (e) Lin W-j (2009) M.S. Thesis, National Sun Yat-sen University, Kaohsiung, Taiwan, ROC

    Google Scholar 

  11. (a) Masamune T, Takasugi M, Murai A, Kobayashi K (1967) J Am Chem Soc 89:4521–4523; (b) Masamune T, Takasugi M, Murai A (1971) Tetrahedron 27:3369–3386

    Google Scholar 

  12. (a) Johnson WS, de Jongh HAP, Coverdale CE, Scott JW, Burckhardt U (1967) J Am Chem Soc 89:4523–4524; (b) Johnson WS, Cox JM, Graham DW, Whitlock HW Jr (1967) J Am Chem Soc 89:4524–4526

    Google Scholar 

  13. Masamune T, Mori Y, Takasugi M, Murai A, Ohuchi S, Sato N, Katsui N (1965) Bull Chem Soc Jpn 38:1374–1378

    Article  CAS  Google Scholar 

  14. (a) Kutney JP, By A, Cable J, Gladstone WAF, Inaba T, Leong SY, Roller P, Torupka EJ, Warnock WDC (1975) Can J Chem 53:1775–1795; (b) Kutney JP, Cable J, Gladstone WAF, Hanssen HW, Nair GV, Torupka EJ, Warnock WDC (1975) Can J Chem 53:1796–1817

    Google Scholar 

  15. Giannis A, Heretsch P, Sarli V, Stößel A (2009) Angew Chem Int Ed 48:7911–7914

    Article  CAS  Google Scholar 

  16. (a) Hirschmann R, Snoddy CS Jr, Wendler NL (1952) J Am Chem Soc 74:2693–2694; (b) Hiskey CF, Hirschmann R, Wendler NL (1953) J Am Chem Soc 75:5135–5136; (c) Hirschmann R, Snoddy CS Jr, Hiskey CF, Wendler NL (1954) J Am Chem Soc 76:4013–4025

    Google Scholar 

  17. (a) Mitsuhashi H, Shibata K (1964) Tetrahedron Lett 5:2281–2283; (b) Mitsuhashi H, Shimizu Y, Moriyama T, Masuda M, Kawahara N (1974) Chem Pharm Bull 22:1046–1052; (c) Mitsuhashi H, Shimizu Y (1961) Tetrahedron Lett 2:777–780

    Google Scholar 

  18. Fu X, Chan T-M, Tann C-H, Thiruvengadam TK (2002) Steroid 67:549–554

    Article  CAS  Google Scholar 

  19. Heretsch P, Rabe S, Giannis A (2010) J Am Chem Soc 132:9968–9969

    Article  CAS  Google Scholar 

  20. Franck RW, Johnson WS (1963) Tetrahedron Lett 4:545–547

    Article  Google Scholar 

  21. (a) Johnson WS, Szmuszkovicz J, Rogier ER, Hadler HI, Wynberg H (1956) J Am Chem Soc 78:6285–6289; (b) Johnson WS, Rogier ER, Szmuszkovicz J, Hadler HI, Ackerman J, Bhattacharyya BK, Bloom BM, Stalmann L, Clement RA, Bannister B, Wynberg H (1956) J Am Chem Soc 78:6289–6302; (c) Franck RW, Johnson WS (1963) Tetrahedron Lett 4:545–547; (d) Johnson WS, Cohen N, Habicht ER Jr, Hamon DPG, Rizzi GP, Faulkner DJ (1968) Tetrahedron Lett 9:2829–2833

    Google Scholar 

  22. (a) Brown E, Lebreton J (1986) Tetrahedron Lett 27:2595–2598; (b) Brown E, Lebreton J (1987) Tetrahedron 43:5827–5840

    Google Scholar 

  23. Ceustermans RAE, Martens HJ, Hoornaert GJJ (1979) J Org Chem 44:1388–1391

    Article  CAS  Google Scholar 

  24. (a) Marsault E, Toró A, Nowak P, Deslongchamps P (2001) Tetrahedron 57:4243–4260; (b) Porco JA Jr, Schoenen FJ, Stout TJ, Clardy J, Schreiber SL (1990) J Am Chem Soc 112:7410–7411; (c) Roush WR, Koyama K, Curtin ML, Moriarty KJ (1996) J Am Chem Soc 118:7502–7512; (d) Vosburg DA, Vanderwal CD, Sorensen EJ (2002) J Am Chem Soc 124:4552–4553; (e) Evans DA, Starr J (2002) Angew Chem Int Ed 41:1787–1790

    Google Scholar 

  25. Ito T, Ito M, Arimoto H, Takamura H, Uemura D (2007) Tetrahedron 48:5465–5469

    Article  CAS  Google Scholar 

  26. (a) Stoker DA (2008) Ph.D. Thesis, University of Nottingham, Nottingham, England; (b) Pattenden G, Gonzalez MA, McCulloch S, Walter A, Woodhead SJ (2004) Proc Natl Acad Sci USA 101:12024–12029

    Google Scholar 

  27. (a) Brennführer A, Neumann H, Beller M (2009) Angew Chem Int Ed 48:4114–4133; (b) Barnard CFJ (2008) Organometallics 27:5402–5422; (c) Skoda-Földes R, Kollár L (2002) Curr Org Chem 6:1097–1119

    Google Scholar 

  28. (a) Tanaka M (1979) Tetrahedron Lett 20:2601–2602; (b) Beletskaya IP (1983) J Organomet Chem 250:551–564; (c) Sheffy FK, Godschalx JP, Stille JK (1984) J Am Chem Soc 106:4833–4840; (d) Goure WF, Wright ME, Davis PD, Labadie SS, Stille JK (1984) J Am Chem Soc 106:6417–6422

    Google Scholar 

  29. (a) Nakanishi W, West FG (2009) Curr Opin Drug Discov Dev 12:732–751; (b) Frontier AJ, Collison C (2005) Tetrahedron 61:7577–7606; (c) Pellissier H (2005) Tetrahedron 61:6479–6517; (d) Tius MA (2005) Eur J Org Chem 2193–2206

    Google Scholar 

  30. (a) Liang G, Xu Y, Seiple IB, Trauner D (2006) J Am Chem Soc 128:11022–11023; (b) He W, Herrick IR, Atesin TA, Caruana PA, Kellenberger CA, Frontier AJ (2008) J Am Chem Soc 130:1003–1011; (c) Marcus AP, Lee AS, Davis RL, Tantillo DJ, Sarpong R (2008) Angew Chem Int Ed 47:6379–6383

    Google Scholar 

  31. (a) Crandall JK, Haseltine RP (1968) J Am Chem Soc 90:6251–6253; (b) Noyori R, Katô M (1968) Tetrahedron Lett 9:5075–5077; (c) Smith AB III, Agosta WC (1973) J Am Chem Soc 95:1961–1968; (d) Leitich J, Heise I, Werner S, Krueger C, Schaffner K (1991) J Photochem Photobiol A Chem 57:127–151; (e) Leitich J, Heise I, Rust J, Schaffner K (2001) Eur J Org Chem 2001:2719–2726

    Google Scholar 

  32. (a) Gao S, Wang Q, Chen C (2009) J Am Chem Soc 131:1410–1412; (b) Gao S, Huang QWLJ-S, Lum L, Chen C (2010) J Am Chem Soc 132:371–383

    Google Scholar 

  33. (a) Liebeskind LS, Fengl RWJ (1990) J Org Chem 55:5359–5364; (b) Farina V, Kapadia S, Krishnan B, Wang C, Liebeskind LSJ (1994) J Org Chem 59:5905–5911; (c) Han X, Stoltz BM, Corey EJ (1999) J Am Chem Soc 121:7600–7605

    Google Scholar 

  34. (a) Takao K-I, Munakata R, Tadano K-I (2005) Chem Rev 105:4779–4807; (b) Keay BA, Hunt IR (1999) Adv Cycloaddit 6:173–210; (c) Roush WR (1990) Adv Cycloaddit 2:91–146; (d) Craig D (1987) Chem Soc Rev 16:187–238

    Google Scholar 

  35. (a) Denmark SE, Heemstra J, John R, Beutner GL (2005) Angew Chem Int Ed 44:4682–4698; (b) Casiraghi G, Zanardi F, Appendino G, Rassu G (2000) Chem Rev 100:1929–1972; (c) Rassu G, Zanardi F, Battistinib L, Casiraghi G (2000) Chem Soc Rev 29:109–118

    Google Scholar 

  36. (a) Neumann CS, Fujimori DG, Walsh CT (2008) Chem Biol 15:99–109; (b) Vaillancourt FH, Yeh E, Vosburg DA, Garneau-Tsodikova S, Walsh CT (2006) Chem Rev 106:3364–3378; (c) Butler A, Walker JV (1993) Chem Rev 93:1937–1944

    Google Scholar 

  37. Chen L (2004) Yin B-l, Xu H-h, Chiu M-h, Wu Y-l. Chin J Chem 22:92–99

    Article  CAS  Google Scholar 

  38. (a) Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562–7563; (b) Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R (1996) J Am Chem Soc 118:2521–2522

    Google Scholar 

  39. (a) Wu X, Li X, Hems W, King F, Xiao J (2004) Org Biomol Chem 2:1818–1821; (b) Wu X, Li X, King F, Xiao J (2005) Angew Chem Int Ed 44:3407–3411; (c) Ohkuma T, Utsumi N, Tsutsumi K, Murata K, Sandoval C, Noyori R (2006) J Am Chem Soc 128:8724–8725

    Google Scholar 

  40. (a) Roush WRJ (1979) J Org Chem 44:4008–4010; (b) Roush WR, Hall SE (1981) J Am Chem Soc 103:5200–5211; (c) Roush WR, Kageyama M, Riva R, Brown BB, Warmus JS, Moriarty KJJ (1991) J Org Chem 56:1192–1210; (d) Taber DF, Gunn BP (1979) J Am Chem Soc 101:3992–3993; (e) Taber DF, Saleh SA (1980) J Am Chem Soc 102:5085–5088; (f) Boeckman RK Jr, Napier JJ, Thomas EW, Sato RIJ (1983) J Org Chem 48:4152–4154; (g) Boeckman RK Jr, Barta TEJ (1985) J Org Chem 50:3421–3423

    Google Scholar 

  41. (a) Katsuki T, Martin VS (1996) Org React 48:1–300; (b) Katsuki T, Sharpless KB (1980) J Am Chem Soc 102:5974–5976; (c) Gao Y, Klunder JM, Hanson RM, Masamune H, Ko SY, Sharpless KB (1987) J Am Chem Soc 109:5765–5780

    Google Scholar 

  42. Maruoka K, Ooi T, Yamamoto H (1989) J Am Chem Soc 111:6431–6432

    Article  CAS  Google Scholar 

  43. Hoveyda AH, Evans DA, Fu GC (1993) Chem Rev 93:1307–1370

    Article  CAS  Google Scholar 

  44. (a) Spaggiari A, Vaccari D, Davoli P, Torre G, Prati FJ (2007) J Org Chem 72:2216–2219; (b) Hoffmann RW, Bovicelli P (1990) Synthesis 657–659

    Google Scholar 

  45. (a) Eggenschwiler JT, Anderson KV (2007) Annu Rev Cell Dev Biol 23:345–373; (b) Quarmby LM, Parker JDK (2005) J Cell Biol 169:707–710

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Chuo Chen .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2012 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gao, S., Chen, C. (2012). Nakiterpiosin. In: Li, J., Corey, E. (eds) Total Synthesis of Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-34065-9_2

Download citation

Publish with us

Policies and ethics