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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 1
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Original Articles

Studies Directed Towards a Practical Synthesis of Brevicomin (III) Cyclization Routes to 6, 8-Dioxabicyclo[3.2.1]octane

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Pages 7-13 | Received 13 Sep 1974, Published online: 05 Dec 2006
 

Abstract

Bicyclic ketals have been noted as an important structural unit in sugars1, an alkaloid2, a terpene3 and in pheromones. It is with regard to this last group that we have been recently directing our attention. Frontalin (1)4 and the brevicomins (2 and 3)5 are sex aggregating pheromones of Dendroctonus frontalisand D. brevicomis, respectively. Because of their potential utility in controlling populations of pine bark beetles, considerable activity has been directed towards their syntheses. 6–10 Particularly in syntheses of brevicomin, where the exo-isomer (2) is the biologically useful isomer for insect control, does the methodology become quite important.

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