Total syntheses of (±)-cis-trikentrin A and (±)-cis-trikentrin B via electrocyclic ring closures of 2,3-divinylpyrrolines

被引：40

作者：

Huntley, Raymond J. ^{[1
]}

Funk, Raymond L. ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

D O I：

10.1021/ol061259a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent and versatile strategy for the diastereoselective syntheses of (+/-)-cis-trikentrin A and B in 10 and 12 steps, respectively, from commercially available N-BOC-2-pyrrolidinone is described. The key step in each of the total syntheses is the construction of the central benzene ring via a facile 6 pi-electrocyclic ring closure of an appropriately substituted 2,3-divinylpyrroline, in turn, readily available by a Stille coupling reaction.

引用

页码：3403 / 3406

页数：4

共 32 条

[1] Total syntheses of (±)-cis-trikentrin A and B.
Huntley, RJ
Funk, RL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U147 - U147
[2] Synthesis of complex indoles: Total syntheses of cis-trikentrin A, cis-trikentrin B, and herbindole B.
Kerr, MA
Banfield, SC
Jackson, SK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U369 - U370
[3] Enantioselective Total Synthesis of cis-Trikentrin B
J Org Chem, 10 (3406):
[4] Total synthesis of (±)-herbindole (±)-cis-trikentrin B
Jackson, SK
Banfield, SC
Kerr, MA
ORGANIC LETTERS, 2005, 7 (07) : 1215 - 1218
[5] Enantioselective total synthesis of cis-trikentrin B
Lee, M
Ikeda, I
Kawabe, T
Mori, S
Kanematsu, K
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10): : 3406 - 3416
[6] Total synthesis of (±)-herbindole A, (±)-herbindole B, and (±)-cis-trikentrin A
Jackson, Stephen K.
Kerr, Michael A.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04): : 1405 - 1411
[7] Asymmetric Hydrovinylation of Vinylindoles. A Facile Route to Cyclopenta[g]indole Natural Products (+)-cis-Trikentrin A and (+)-cis-Trikentrin B
Liu, Wang
Lim, Hwan Jung
RajanBabu, T. V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) : 5496 - 5499
[8] Concise Total Synthesis of (±)-cis-Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne Cycloaddition
Buszek, Keith R.
Brown, Neil
Luo, Diheng
ORGANIC LETTERS, 2009, 11 (01) : 201 - 204
[9] Meso-desymmetrization approach toward the total synthesis of cis-trikentrin A and herbindole B
Leal, Raul A.
Lee, Youjin
Sarpong, Richmond
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[10] ORGN 519-Total synthesis of (±)-cis-trikentrin and the herbindoles via indole aryne cycloaddition
Brown, Neil
Luo, Diheng
Buszek, Keith R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236

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