A Synthesis of Methyl 2α-Acetoxy-3-deoxo-3α-hydroxyangolensate
The title compound (1a) has been partially synthesised from gedunin.It is the first natural 1α,2α,3α-trihydroxy terpene molecule to have been synthesised.Attempts to introduce a 2α-hydroxy group into a preformed methyl angolensate derivative failed, and the synthesis was achieved by the prior preparation of 2α-acetoxy-7-deacetoxy-7-oxokhivorin (2a), which was converted into the title compound.The key stage in the conversion is the Baeyer-Villiger oxidation of the 7-oxo group to a lactone, which was studied in some detail.The use of buffered peracetic acid effects the required oxidation in good yield without oxidising the furan ring; the use of pertrifluoroacetic acid oxidises the furan ring to an unsaturated lactone without attacking the carbonyl group.The implications of this are considered in an Appendix.
Kehrli, Anne R. H.,Taylor, David A. H.
p. 2067 - 2070
(2007/10/02)
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