A diastereoselective total synthesis of trans-trikentrin A: a ring contraction approach.
作者： Luiz F. Silva , Marcus V. Craveiro
DOI: 10.1021/OL8023105
关键词:
摘要: A new route to obtain the polyalkylated indole (±)-trans-trikentrin was developed. The synthesis of this natural alkaloid features a thallium(III)-mediated ring contraction reaction trans-1,3-disubstituted five-membered in diastereoselective manner. Thallium(III) is chemoselective rearrangement, reacting with olefin without oxidation moiety. Other key transformations are Bartoli’s construct heterocyclic and Heck coupling add carbons atom that will originate nonaromatic cycle.
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Robert J. Capon, John K. Macleod, Peter J. Scammells, The trikentrins: novel indoles from the sponge Trikentrion flabelliforme Tetrahedron. ,vol. 42, pp. 6545- 6550 ,(1986) , 10.1016/S0040-4020(01)88117-5
Luiz F. Silva, Construction of cyclopentyl units by ring contraction reactions Tetrahedron. ,vol. 58, pp. 9137- 9161 ,(2002) , 10.1016/S0040-4020(02)00990-0
J. Scott Sawyer, Douglas W. Beight, Edward C. R. Smith, David W. Snyder, Marcia K. Chastain, Richard L. Tielking, Lawrence W. Hartley, Donald G. Carlson, Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA2 Journal of Medicinal Chemistry. ,vol. 48, pp. 893- 896 ,(2005) , 10.1021/JM0401309
Takanori Yasukouchi, Ken Kanematsu, The total synthesis of (±)-cis-trikentrin B via allene intramolecular cycloaddition Tetrahedron Letters. ,vol. 30, pp. 6559- 6562 ,(1989) , 10.1016/S0040-4039(01)89021-3
Avijit Banerji, Gopa Nandi, Metal Reagents in Organic Reactions: Part V — Reactions of Coumarins with Thallium (III) Salts Heterocycles. ,vol. 26, pp. 1221- 1226 ,(1987) , 10.3987/R-1987-05-1221
Pietro Passacantilli, A new entry into versatile ring opening of O-benzyl glycals and related compounds via Tl(NO3)3 and NaBH4 Tetrahedron Letters. ,vol. 30, pp. 5349- 5352 ,(1989) , 10.1016/S0040-4039(01)93784-0
Hiromitsu Takayama, Kaori Misawa, Naoki Okada, Hayato Ishikawa, Mariko Kitajima, Yoshio Hatori, Toshihiko Murayama, Sumphan Wongseripipatana, Kimihito Tashima, Kenjiro Matsumoto, Syunji Horie, New Procedure to Mask the 2,3-π Bond of the Indole Nucleus and Its Application to the Preparation of Potent Opioid Receptor Agonists with a Corynanthe Skeleton Organic Letters. ,vol. 8, pp. 5705- 5708 ,(2006) , 10.1021/OL062173K
Laurence Saugé, Nathalie Ayerbe, Gérard Coudert, Jean-Yves Mérour, Sylvain Routier, A mild and selective method for N-Boc deprotection Tetrahedron Letters. ,vol. 43, pp. 589- 591 ,(2002) , 10.1016/S0040-4039(01)02225-0
Yasuhiro Wada, Hideo Nagasaki, Masao Tokuda, Kazuhiko Orito, Synthesis of N-protected staurosporinones. Journal of Organic Chemistry. ,vol. 72, pp. 2008- 2014 ,(2007) , 10.1021/JO062184R
Raymond J. Huntley, Raymond L. Funk, Total syntheses of (+/-)-cis-trikentrin A and (+/-)-cis-trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines. Organic Letters. ,vol. 8, pp. 3403- 3406 ,(2006) , 10.1021/OL061259A