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The total synthesis of d1-dihydrocallitrisin

✍ Scribed by Jollie D. Godfrey; Arthur G. Schultz

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 205 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95373-0

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✦ Synopsis

Bromodiene 2 is converted to dl-dihydrocallitrisin (l), a sesquiterpene lactone recently isolated from the heartwood oFCa11itris columellari?. We wish to describe the total synthesis of $I_-dihydrocallitrisin (1_), a new sesquiterpene lactone isolated by Carman and Brecknell from the heartwood of Callitris columellaris.L The structure of dihydrocallitrisin is extremely interesting because of the novel stereochemical relationship between C(7), C(8) and C(10). Prior to the report of the isolation of 1, we were not aware of any natural eudesmane-like sesquiterpene which incorporated this relative stereochemistry. Structural confirmation by total synthesis of 1 is now provided.

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