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Synthetic transformation of santonin into (5α,7α,11β)-3,6-dioxogermacr-1-en-13,7-olide, a new intermediate for germacranes and guaianes

✍ Scribed by Harapanhalli, Ravi S.

Publisher: John Wiley and Sons
Year: 1988
Tongue: English
Weight: 383 KB
Volume: 1988
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198819881016

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✦ Synopsis

A seven-step synthesis of a new intermediate (5a,fa,llfi)-3,6dioxogermacr-l-cn-l3,7-olide (10) is describcd starting from [ -)-~-santonin (I). The key stcp in thc transformation was photolytic skclctal rearrangement of (4qSP,601,11 F)-S-hydroxy-2oxoeudesman-l3.6-olide (9) to the W e compound, scnsitised by mercuric oxide and iodine.

The skeletal rearrangement of santonin (1) and compounds derived from it is a matter of continued interest in the synthesis of novel precursors for sesquiterpenes belonging to germacranel) and guaiane*) types. The former are of particular interest for being possible biogenetic links ' 1 between farnesol and polycarbocyclic ses-15

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