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An enolate-accelerated cope rearrangement

✍ Scribed by Paul A. Wender; Robert J. Ternansky; Scott McN. Sieburth

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 256 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98723-9

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✦ Synopsis

The first example of an enolate accelerated Cope rearrangement is described along with its importance in the rearrangement of S-alkoxy-deca-1,3,7,9_tetraenes.

We recently introduced a macroexpansion method' for the synthesis of large ring compounds, exemplified by the conversion of 1 into 4(Scheme I) which has resulted in straightforward syntheses of (+)-muscone ( 5)" and (-)-3X-cembrene A (6)ld.

While the precise mechanism for this rearrangement could not be SCHEME I 4 c5 0 5

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