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.
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References
(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
(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
(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
(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
(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
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
(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
(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
(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
(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
(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
(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
Masamune T, Mori Y, Takasugi M, Murai A, Ohuchi S, Sato N, Katsui N (1965) Bull Chem Soc Jpn 38:1374–1378
(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
Giannis A, Heretsch P, Sarli V, Stößel A (2009) Angew Chem Int Ed 48:7911–7914
(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
(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
Fu X, Chan T-M, Tann C-H, Thiruvengadam TK (2002) Steroid 67:549–554
Heretsch P, Rabe S, Giannis A (2010) J Am Chem Soc 132:9968–9969
Franck RW, Johnson WS (1963) Tetrahedron Lett 4:545–547
(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
(a) Brown E, Lebreton J (1986) Tetrahedron Lett 27:2595–2598; (b) Brown E, Lebreton J (1987) Tetrahedron 43:5827–5840
Ceustermans RAE, Martens HJ, Hoornaert GJJ (1979) J Org Chem 44:1388–1391
(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
Ito T, Ito M, Arimoto H, Takamura H, Uemura D (2007) Tetrahedron 48:5465–5469
(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
(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
(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
(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
(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
(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
(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
(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
(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
(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
(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
Chen L (2004) Yin B-l, Xu H-h, Chiu M-h, Wu Y-l. Chin J Chem 22:92–99
(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
(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
(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
(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
Maruoka K, Ooi T, Yamamoto H (1989) J Am Chem Soc 111:6431–6432
Hoveyda AH, Evans DA, Fu GC (1993) Chem Rev 93:1307–1370
(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
(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
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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
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