Applications of ring closing metathesis. Total synthesis of (±)-pseudotabersonine

被引：14

作者：

Cheng, Bo ^{[1
]}

Sunderhaus, James D. ^{[1
]}

Martin, Stephen F. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2015年 / 71卷 / 39期

基金：

美国国家卫生研究院;

关键词：

Double ring-closing metathesis; Multicomponent assembly process; Alkaloid; Total synthesis; MULTICOMPONENT ASSEMBLY PROCESSES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; HIGHLY EFFICIENT; FACILE SYNTHESES; MANZAMINE-A; ALKALOIDS; DIVERSE; STRATEGY; CONSTRUCTION;

D O I：

10.1016/j.tet.2015.04.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel approach to the Aspidosperma family of alkaloids was developed and applied to a concise total synthesis of (+/-)-pseudotabersonine that was accomplished in 11 steps. Key transformations include a stepwise variant of a Mannich-like multicomponent assembly process, a double ring-closing metathesis sequence, and a one-pot deprotection/cyclization reaction. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7323 / 7331

页数：9

共 62 条

[21] Multicomponent Assembly Processes for the Synthesis of Diverse Yohimbine and Corynanthe Alkaloid Analogues
Granger, Brett A.
Wang, Zhigian
Kaneda, Kyosuke
Fang, Zhenglai
Martin, Stephen F.
[J]. ACS COMBINATORIAL SCIENCE, 2013, 15 (07) : 379 - 386
[22] Libraries of 2,3,4,6,7,11b-Hexahydro-1H-pyrido[2,1-a]isoquinolin-2-amine Derivatives via a Multicomponent Assembly Process/1,3-Dipolar Cycloaddition Strategy
Granger, Brett A.
Kaneda, Kyosuke
Martin, Stephen F.
[J]. ACS COMBINATORIAL SCIENCE, 2012, 14 (01) : 75 - 79
[23] Multicomponent Assembly Strategies for the Synthesis of Diverse Tetrahydroisoquinoline Scaffolds
Granger, Brett A.
Kaneda, Kyosuke
Martin, Stephen F.
[J]. ORGANIC LETTERS, 2011, 13 (17) : 4542 - 4545
[24] Grubbs R.H., 2003, HDB METATHESIS, P1
[25] Multicomponent, Mannich-type assembly process for generating novel, biologically-active 2-arylpiperidines and derivatives
Hardy, Simon
Martin, Stephen F.
[J]. TETRAHEDRON, 2014, 70 (40) : 7142 - 7157
[26] Multicomponent Assembly and Diversification of Novel Heterocyclic Scaffolds Derived from 2-Arylpiperidines
Hardy, Simon
Martin, Stephen F.
[J]. ORGANIC LETTERS, 2011, 13 (12) : 3102 - 3105
[27] Enantioselective total syntheses of manzamine A and related alkaloids
Humphrey, JM
Liao, YS
Ali, A
Rein, T
Wong, YL
Chen, HJ
Courtney, AK
Martin, SF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) : 8584 - 8592
[28] Total synthesis of (+)-ambruticin S
Kirkland, TA
Colucci, J
Geraci, LS
Marx, MA
Schneider, M
Kaelin, DE
Martin, SF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12432 - 12433
[29] A general strategy to Aspidosperma alkaloids:: Efficient, stereocontrolled synthesis of tabersonine
Kozmin, SA
Rawal, VH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) : 13523 - 13524
[30] STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .16. SYNTHESES OF D/E TRANS AND CIS DESETHYLVINCADIFFORMINES AND OF THE C16 EPIMERIC CARBOMETHOXYDESETHYLDIHYDROCLEAVAMINES AND THEIR ISOLABLE PIPERIDINE RING CONFORMATIONAL ISOMERS
KUEHNE, ME
ZEBOVITZ, TC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) : 4331 - 4339

← 1 2 3 4 5 6 7 →