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Synthesis of (-)-astrogorgiadiol
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
The Journal of Organic Chemistry
|June 30, 2001
Abstract:
Reaction of Rh2(S)-PTPA4 with the (R)-citronellol-derived alpha-diazo-beta-ketoester 1 led to the formation of cyclic beta-ketoester 2 in 95% yield and 48% diastereomeric excess. The purity of 2 was increased to > 99% de after one crystallization. To demonstrate its utility in steroid total synthesis, the beta-ketoester 2 was carried on to secosteroid (-)-astrogorgiadiol (3), a naturally occurring vitamin D analogue with antiproliferative properties.