A vinylogous urethane approach towards the synthesis of okadaic acid. Construction of the C9-C18 fragment. Part II.

被引：21

作者：

Dankwardt, SM ^{[1
]}

Dankwardt, JW ^{[1
]}

Schlessinger, RH ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 28期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)00972-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereo- and enantioselective acylation-reduction sequence of a vinylogous urethane lactone silylketene acetal sets the initial stereocenter in this approach towards the C9-C18 fragment of okadaic acid. The remainder of the stereocenters are installed via a silyl cuprate conjugate addition trapping sequence, and a lactol is transformed to a tetrahydrofuran by addition of a propargyl aluminum species. A novel tetrahydrofuran ring opening reaction utilizing dimethyl boron bromide is also illustrated. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4975 / 4978

页数：4

共 17 条

[1] THE CONJUGATE ADDITION OF A SILYL GROUP TO ENONES AND ITS REMOVAL WITH COPPER(II) BROMIDE - A PROTECTING GROUP FOR THE ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES [J].