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Synthesis of endo-1,3-dimethyl-2,9-dioxa-bicyclo [3.3.1.] nonane

✍ Scribed by Peter Mohr; Christoph Tamm

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
112 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title compound has been synthesized stereoselectively based on a new methodology for the construction of erythro-1,3-diols. Endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane (11, first isolated by Heemann and Francke in 1976 from Norway spruce attacked by the ambrosia beetle (Tgypodendron Lineatum Oliv.)', -__--__-^_______ was proved to exhibit an important role for causing host selection. Several groups have reported syntheses for 1. in racemic or optically active form2. In a preceding letter we have proposed a stereoselective method for the construction of erythro-1,3-diols based on the V5+ -catalyzed TBHP-epoxidation of (Z)-5-hydroxy-2-alkenylsilanes 3 . In this

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