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Stereocontrolled approach to highly substituted cyclopentanones. Application in a formal synthesis of Δ9(12)-capnellene

✍ Scribed by Susanta Samajdar; Debasis Patra; Subrata Ghosh

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 697 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)10387-8

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✦ Synopsis

A direct stereocontrolled route for the construction of highly substituted cyclopentanones 10a-d has been developed starting from aeyclic ketones 5a,b. The key step involves copper(I)-eatalysed stezeoselective photocycloaddition of the dienes 6a-d followed by stereospecific rearrangement of the cyclobutane derivatives 7a,b, 8 and 9. Employing this methodology a formal synthesis of the sesquiterpene Ag~12)-capnellene 2 has been achieved.

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