Enantioselective total synthesis of δ-lactonic marine natural products, (+)-tanikolide and (-)-malyngolide, via RCM reaction

被引：52

作者：

Mizutani, H ^{[1
]}

Watanabe, M ^{[1
]}

Honda, T ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 44期

关键词：

ring-closing metathesis; (+)-tanikolide; (-)-malyngolide; marine natural product; lactonic compound;

D O I：

10.1016/S0040-4020(02)01160-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective total synthesis of delta-lactonic marine natural products, (+)-tanikolide and (-)-malyngolide isolated from Lyngbya majuscula, was achieved by using the Sharpless asymmetric epoxidation and a ring-closing metathesis, as key reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8929 / 8936

页数：8

共 28 条

[1] A stereoselective synthesis of (+)-malyngolide via a ring-closing olefin metathesis [J].

Carda, M ;

Castillo, E ;

Rodríguez, S ;

Marco, JA .

TETRAHEDRON LETTERS, 2000, 41 (29) :5511-5513

[2] STRUCTURE AND ABSOLUTE-CONFIGURATION OF MALYNGOLIDE, AN ANTIBIOTIC FROM THE MARINE BLUE-GREEN-ALGA LYNGBYA-MAJUSCULA GOMONT [J].

CARDLLINA, JH ;

MOORE, RE ;

ARNOLD, EV ;

CLARDY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4039-4042

[3] Synthesis of functionalized olefins by cross and ring-closing metatheses [J].

Chatterjee, AK ;

Morgan, JP ;

Scholl, M ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784

[4] Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].

Chatterjee, AK ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (11) :1751-1753

[5]

Finn M. G., 1985, ASYMMETRIC SYNTHESIS, V5, P247

[6]

Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012

[7] Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts [J].

Garber, SB ;

Kingsbury, JS ;

Gray, BL ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8168-8179

[8] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[9] Asymmetric hetero Diels-Alder route to quaternary carbon centers: synthesis of (-)-malyngolide [J].

Ghosh, AK ;

Shirai, M .

TETRAHEDRON LETTERS, 2001, 42 (36) :6231-6233

[10] RING-CLOSING METATHESIS AND RELATED PROCESSES IN ORGANIC-SYNTHESIS [J].

GRUBBS, RH ;

MILLER, SJ ;

FU, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (11) :446-452

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