Bicyclo[10.2.1]pentadecenone derivatives by free radical macrocyclisation

Jeremy Robertson, Jeremy N. Burrows, Paul A. Stupple

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Abstract

The synthesis of intermediates for the preparation of stereoisomeric bicyclo[10.2.1]pentadec-13-en-3-ones is described. The preparation and the addition of 6-functionalised hexylcuprate reagents to bicyclic lactone 5 is discussed and a method described for the epimerisation of the so-formed trans-disubstituted cyclopentene derivatives. The cis- and trans-1,4-disubstituted cyclopentenes are both shown to undergo 13-endo-trig cyclisation affording the title bicyclic compounds in moderate yield.

Original languageEnglish
Pages (from-to)14807-14820
Number of pages14
JournalTetrahedron
Volume53
Issue number43
DOIs
Publication statusPublished - 27 Oct 1997
Externally publishedYes

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