130877-21-3Relevant academic research and scientific papers
A Synthesis of Methyl 2α-Acetoxy-3-deoxo-3α-hydroxyangolensate
Kehrli, Anne R. H.,Taylor, David A. H.
, p. 2067 - 2070 (2007/10/02)
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.
