Jurnal Matematika & Sains
Vol 14, No 4 (2009)

Stereoselektivitas Reaksi Aldol dalam Sintesis C1-C12 Senyawa Epotilon

Muharram Muharram ( Jurusan Kimia FMIPA Universitas Negeri Makassar)
Dieter Schinzer ( Department of Chemistry FVS Otto-Von-Goericke-Universitaet Magderburg)



Article Info

Publish Date
17 Jun 2010

Abstract

The retrosynthesis analysis shows that the synthesis of epothilone is built from three main fragments, which are ethyl ketone 5, thiazole 3, and aldehyde 4 fragments. The three fragments are coupled by aldol reaction, esterification or macrolactonisation, and olefin-epoxide metathesis. The aldol reaction was conducted in synthesis of C1-C12 epothilone from ethyl ketone 5 and chiral aldehyde 4a with highly stereoselective (97% ee) at temperature -78 °C and used lithium diisopropylamine (LDA) as a base. The ethyl ketone was synthesized from the α-bromoester 10 and diethyl ketone 11 with a good yield in each of eight stages of reaction. The chiral aldehyde 4a was synthesized from 6-heptenoic acid 19 through  six steps reaction and Evans-Auxiliary 21.

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