Efficient Approach to Fluvirucins B2-B5, Sch 38518, and Sch 39185. First Synthesis of their Aglycon, via CM and RCM Reactions

被引：22

作者：

Llacer, Enric ^{[1
]}

Urpi, Felix ^{[1
]}

Vilarrasa, Jaume ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Fac Quim, E-08028 Barcelona, Catalonia, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

INFLUENZA-A VIRUS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; 2ND-GENERATION TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; OLEFIN CROSS-METATHESIS; FORMAL TOTAL-SYNTHESIS; PHYSICOCHEMICAL PROPERTIES; ANTHELMINTIC MACROLACTAMS; STRUCTURE ELUCIDATION; ASYMMETRIC-SYNTHESIS;

D O I：

10.1021/ol901030f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A route to fluvirucinins B2-5 (the common aglycon of fluvirucins B-2-B-5, Sch 38518, and Sch 39185) is reported for the first time. A ring-closing metathesis (RCM) generated the C6-C7 double bond, which by catalytic hydrogenation (in toluene) gave the desired epimer with a 9:1 diastereoselection. Azide 8a and carboxylic acid 5 came from ethyl-branched fragments C9-C13 (CHO at C9) and C1-C5 via an asymmetric allylation of the former and a cross metathesis (CM) followed by a ketone methylenation (with 20 mol % of DMF as a sacrificial additive) of the latter.

引用

页码：3198 / 3201

页数：4

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