Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B

被引：16

作者：

Chegondi, Rambabu ^{[1
]}

Tan, Mary M. L. ^{[1
]}

Hanson, Paul R. ^{[1
]}

机构：

[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 10期

关键词：

V-ATPASE INHIBITORS; DOLABELIDES A-D; SALICYLIHALAMIDE-A; METATHESIS CATALYSTS; OLEFIN METATHESIS; CROSS-METATHESIS; GENERATION; RUCL2(=CHR)(PR(3))(2); ACTIVATION; ALCOHOLS;

D O I：

10.1021/jo200337v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise formal synthesis of the cytotoxic macrolides (-)-salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4 steps), a 13-step route and a more efficient 9-step sequence relying on regioselective esterification of a key diol.

引用

页码：3909 / 3916

页数：8

共 44 条

[1]

Boyd MR, 2001, J PHARMACOL EXP THER, V297, P114

[2] A general model for selectivity in olefin cross metathesis [J].