Synthesis of (−)-Astrogorgiadiol

Synthesis of (−)-Astrogorgiadiol

Reaction of Rh2(S)-PTPA4 with the (R)-citronellol-derived α-diazo-β-ketoester 1 led to the formation of cyclic β-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 β...

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Veröffentlicht in:Journal of organic chemistry 2001-02, Vol.66 (3), p.944-953
Hauptverfasser: Taber, Douglass F, Malcolm, Scott C
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Catalysis
Spectrum Analysis
Vitamin D - analogs & derivatives
Vitamin D - chemical synthesis
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container_title Journal of organic chemistry
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creator Taber, Douglass F
Malcolm, Scott C
description Reaction of Rh2(S)-PTPA4 with the (R)-citronellol-derived α-diazo-β-ketoester 1 led to the formation of cyclic β-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 β-ketoester 2 was carried on to secosteroid (−)-astrogorgiadiol (3), a naturally occuring vitamin D analogue with antiproliferative properties.
doi_str_mv 10.1021/jo001519g
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subjects Catalysis
Spectrum Analysis
Vitamin D - analogs & derivatives
Vitamin D - chemical synthesis
title Synthesis of (−)-Astrogorgiadiol
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