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A Convergent Synthesis of (±)-α- and β-Himachalenes

✍ Scribed by Wolfgang Oppolzer; Roger L. Snowden

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
381 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

(±)‐α and β‐Himachalene, 5 and 6, have been synthesized in a convergent manner from 3,3‐dimethylacrolein (9), the ester enolate 10 and the silyloxypentadienyllithium 7. The key steps are the regioselective γ‐addition of the dienal 13 to 7 and the intramolecular Diels‐Alder addition 15 → 16. Hydrogenolysis of the diethylphosphate group and functionalization at C (5) completed the synthesis of 5 and 6.

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