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

[1] Adrade R. B., 2005, ORG LETT, V7, P5733
[2] Alvaro G, 2000, SYNTHESIS-STUTTGART, P581
[3] Synthesis of (-)-Pseudotabersonine, (-)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow
Beatty, Joel W.
Stephenson, Corey R. J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) : 10270 - 10273
[4] Diels-Alder reactions of N-tosyl-3-nitroindole and dienamides:: synthesis of intermediates of Aspidospermine alkaloids
Biolatto, B
Kneeteman, M
Mancini, P
[J]. TETRAHEDRON LETTERS, 1999, 40 (17) : 3343 - 3346
[5] A COMMON INTERMEDIATE PROVIDING SYNTHESES OF PSI-TABERSONINE, CORONARIDINE, IBOXYPHYLLINE, IBOPHYLLIDINE, VINAMIDINE, AND VINBLASTINE
BORNMANN, WG
KUEHNE, ME
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1752 - 1760
[6] Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis
Brenneman, JB
Machauer, R
Martin, SF
[J]. TETRAHEDRON, 2004, 60 (34) : 7301 - 7314
[7] BIOMIMETIC TOTAL SYNTHESIS OF PSEUDOTABERSONINE - A NOVEL OXINDOLE-BASED APPROACH TO CONSTRUCTION OF ASPIDOSPERMA ALKALOIDS
CARROLL, WA
GRIECO, PA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) : 1164 - 1165
[8] A general model for selectivity in olefin cross metathesis
Chatterjee, AK
Choi, TL
Sanders, DP
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
[9] Concise Total Synthesis of (±)-Pseudotabersonine via Double Ring-Closing Metathesis Strategy
Cheng, Bo
Sunderhaus, James D.
Martin, Stephen F.
[J]. ORGANIC LETTERS, 2010, 12 (16) : 3622 - 3625
[10] Cordell G.A., 1979, ALKALOIDS, V17, P199

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