AN ALKYLATIVE STRATEGY TO THE C-13 TO C-21 SECTOR OF DISCODERMOLIDE

被引：34

作者：

YANG, G ^{[1
]}

MYLES, DC ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES, DEPT CHEM & BIOCHEM, LOS ANGELES, CA 90024 USA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)76205-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the C-13 to C-21 sector of the immunosuppressive marine natural product discodermolide (1) is described. The C-15 to C-16 bond is formed by diastereoselective alkylation of a ketone enolate. Either diastereomer of allkylation Can be obtained by selecting the appropriate counter ion. The C-16 to C-21 subunit is prepared in two steps from 11.

引用

页码：1313 / 1316

页数：4

共 8 条

[1] STUDIES ON THE ALKYLATION OF CHIRAL ENOLATES - APPLICATION TOWARD THE TOTAL SYNTHESIS OF DISCODERMOLIDE [J].

CLARK, DL ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5878-5879

[2]

EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P1

[3] DISCODERMOLIDE - A NEW BIOACTIVE POLYHYDROXYLATED LACTONE FROM THE MARINE SPONGE DISCODERMIA-DISSOLUTA [J].

GUNASEKERA, SP ;

GUNASEKERA, M ;

LONGLEY, RE ;

SCHULTE, GK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4912-4915

[4] ALLYLIC STRAIN IN 6-MEMBERED RINGS [J].

JOHNSON, F .

CHEMICAL REVIEWS, 1968, 68 (04) :375-+

[5] DISCODERMOLIDE - A NEW, MARINE-DERIVED IMMUNOSUPPRESSIVE COMPOUND .1. INVITRO STUDIES [J].

LONGLEY, RE ;

CADDIGAN, D ;

HARMODY, D ;

GUNASEKERA, M ;

GUNASEKERA, SP .

TRANSPLANTATION, 1991, 52 (04) :650-656

[6] DISCODERMOLIDE - A NEW, MARINE-DERIVED IMMUNOSUPPRESSIVE COMPOUND .2. INVIVO STUDIES [J].

LONGLEY, RE ;

CADDIGAN, D ;

HARMODY, D ;

GUNASEKERA, M ;

GUNASEKERA, SP .

TRANSPLANTATION, 1991, 52 (04) :656-661

[7] ALDOL STRATEGY - COORDINATION OF THE LITHIUM CATION WITH AN ALKOXY SUBSTITUENT [J].

MASAMUNE, S ;

ELLINGBOE, JW ;

CHOY, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (20) :5526-5528

[8] STEREOSELECTIVE REDUCTION OF BETA-ALKOXY KETONES - A SYNTHESIS OF SYN-1,3-DIOLS [J].

MORI, Y ;

KUHARA, M ;

TAKEUCHI, A ;

SUZUKI, M .

TETRAHEDRON LETTERS, 1988, 29 (42) :5419-5422

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