Asymmetric synthesis of a C1-C19 fragment of ulapualide A

被引：13

作者：

Celatka, CA

Panek, JS

机构：

[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Streamlined Synthesis, Boston, MA 02215 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 39期

关键词：

marine metabolites; tris-oxazole; ulapualide A;

D O I：

10.1016/S0040-4039(02)01553-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled synthesis of a C1-C19 fragment of ulapualide A has been accomplished. The C3 hydroxyl-bearing stereocenter was established by Jacobsen's hydrolytic kinetic resolution (HKR) of a terminal epoxide. while the C9 methyl stereocenter was introduced through an asymmetric crotylation using chiral organosilane (S)-7. Union of the C1-C6 and the C7-C19 fragments by a Kishi-Nozaki coupling, followed by oxidation and conjugate addition of hydride completed the preparation of the fragment. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7043 / 7046

页数：4

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