Total Synthesis of Grandisine D

被引：36

作者：

Kurasaki, Haruaki ^{[2
]}

Okamoto, Iwao ^{[1
]}

Morita, Nobuyoshi ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

[2] Kyorin Pharmaceut Co Ltd, Discovery Res Labs, Nogi, Tochigi 3290114, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 05期

关键词：

BAYLIS-HILLMAN REACTION; LEWIS-BASE ORGANOCATALYST; TREE ELAEOCARPUS-GRANDIS; CHIRAL BRONSTED ACIDS; ABSOLUTE-CONFIGURATION; INDOLIZIDINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; CHEMISTRY; IONS;

D O I：

10.1021/ol900032h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of grandisine D (5) was achieved by a Bronsted acid mediated Morita-Baylis-Hillman (MBH) ring-closure reaction and stereoselective aldol condensation with (S)-5-methylcyclohexenone (9) as key steps. The MBH approach was also applicable for the construction of the aza-fused bicyclic systems of pyrrolizidine and stemona alkaloids.

引用

页码：1179 / 1181

页数：3

共 28 条

[21] Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis [J].

Myers, Eddie L. ;

de Vries, Johannes G. ;

Aggarwal, Varinder K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (11) :1893-1896

[22] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[23] ENANTIOSELECTIVE TOTAL SYNTHESIS OF NATURAL (+)-LUCIDULINE [J].

OPPOLZER, W ;

PETRZILKA, M .

HELVETICA CHIMICA ACTA, 1978, 61 (08) :2755-2762

[24] Recent progress in the chemistry of the Stemona alkaloids [J].

Pilli, RA ;

de Oliveira, MDCF .

NATURAL PRODUCT REPORTS, 2000, 17 (01) :117-127

[25] ANALOGS OF THE IBOGA ALKALOIDS - SYNTHESIS AND REACTIONS OF (+/-)-15-OXO-20-DEETHYLCORONARIDINE DERIVATIVES [J].

SUNDBERG, RJ ;

AMAT, M ;

FERNANDO, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3151-3159

[26] A PRACTICAL PREPARATION OF THE INDOLIZIDINE NUCLEUS - SYNTHESIS OF (+/-)-ELAEOKANINE-A [J].

TABER, DF ;

HOERRNER, RS ;

HAGEN, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1287-1289

[27] ALPHA-ACYLIMINIUM ION SYNTHESIS OF ELAEOKANINE-B [J].

WIJNBERG, BP ;

SPECKAMP, WN .

TETRAHEDRON LETTERS, 1981, 22 (50) :5079-5082

[28] Efficient Baylis-Hillman reactions promoted by mild cooperative catalysts and their application to catalytic asymmetric synthesis [J].

Yamada, YMA ;

Ikegami, S .

TETRAHEDRON LETTERS, 2000, 41 (13) :2165-2169

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