Total synthesis of the threo, trans, threo-mono-tetrahydrofuran annonaceous acetogenin longifolicin

被引：39

作者：

Marshall, JA ^{[1
]}

Jiang, HJ ^{[1
]}

机构：

[1] Univ Virginia, Dept Chem, Charlottesville, VA 22901 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(98)00007-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of the C-35 threo, trans, threo-mono-tetrahydrofuran annonaceous acetogenin longifolicin through use of chiral long-chain alpha- and gamma-OMOM allylic stannanes and (E)-ethyl 3-formyl-2-propenoate as the starting materials is described. The synthesis is structurally definitive and potentially applicable to other members of this family of cytotoxic acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1493 / 1496

页数：4

共 14 条

[11] ASYMMETRIC DIHYDROXYLATION OF PRIMARY ALLYLIC HALIDES AND A CONCISE SYNTHESIS OF (-)-DIEPOXYBUTANE
VANHESSCHE, KPM
WANG, ZM
SHARPLESS, KB
[J]. TETRAHEDRON LETTERS, 1994, 35 (21) : 3469 - 3472
[12] CARBOHYDRATES AS A PRACTICAL SOURCE OF CHIRAL POLYHYDROXY ACETYLENES
YADAV, JS
CHANDER, MC
RAO, CS
[J]. TETRAHEDRON LETTERS, 1989, 30 (40) : 5455 - 5458
[13] Longifolicin, longicoricin, and gigantetroneninone, three novel bioactive mono-tetrahydrofuran annonaceous acetogenins from Asimina longifolia (Annonaceae)
Ye, Q
Alfonso, D
Evert, D
McLauglin, JL
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (04) : 537 - 545
[14] Recent advances in annonaceous acetogenins
Zeng, L
Ye, Q
Oberlies, NH
Shi, G
Gu, ZM
He, K
McLaughlin, JL
[J]. NATURAL PRODUCT REPORTS, 1996, 13 (04) : 275 - 306

← 1 2 →