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Terpenoids—L:Transformation products of costunolide

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
20
Issue
5
Identifiers
DOI: 10.1016/s0040-4020(01)98994-x

Abstract

Abstract Costunolide, containing a ten-membered carbocyclic ring system with the unique distribution of double bonds, undergoes many interesting transformations. The diol prepared by lithium aluminium hydride reduction of costunolide when subjected to metal amine reduction gives a hydrocarbon, C 15H 26, a secondary alcohol, C 15H 26O, and a primary alcohol, C 15H 26O, and a primary alcohol, C 15H 26O to which structures, VIII, X and XII have been assigned on the basis of spectral data and their conversions to elemene-type products on pyrolysis and to mono-ethenoid bicyclic products on acid catalysed cyclization. The secondary alcohol X has been converted to d-junenol which constitutes a new synthesis of the alcohol from costunolide. Pyrolysis and acid catalysed cyclization of 12-methoxydihydrocostunolide have also been described.

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