Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones - Tools and tactics for solving problems in fluorous mixture synthesis

被引：37

作者：

Dandapani, S ^{[1
]}

Jeske, M ^{[1
]}

Curran, DP ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 23期

关键词：

D O I：

10.1021/jo051526a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of fluorous mixture synthesis (FMS) for accessing natural products and their stereoisomers was validated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone. Four fluorous p-methoxybenzyl groups were used as tags, and a "4-mix-4-split" approach was employed in a divergent synthesis. This paper presents the details of the FMS of pine sawfly sex pheromones with an emphasis on identification and solving of problems encountered when working with fluorous mixtures.

引用

页码：9447 / 9462

页数：16

共 31 条

[1]

Bellingham R, 1996, SYNTHESIS-STUTTGART, P285

[2] The sex pheromone of the pine sawfly Microdiprion pallipes (Hymenoptera: Diprionidae) [J].