A new, efficient synthesis of (+)-isodrimenin
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1163-1164
- https://doi.org/10.1039/p19820001163
Abstract
A new, efficient synthesis of natural (+)-isodrimenin (1a) from manool is reported. This synthesis consists of the following key steps. The cyclic peroxide (3), obtained from the diene (2) by photo-oxygenation in meso-tetraphenylporphine in carbon tetrachloride, was epoxidised to protect the Δ8.9-double bond. The epoxy-peroxide (5) thus obtained smoothly underwent ferrous sulphate-catalysed rearrangement to the epoxy-lactol (6a), which on oxidation with Sarett reagent led to the epoxy-lactone (6b). Deoxygenation of (6b) with pentacarbonyliron in N,N-dimethylacetamide afforded the α,β-unsaturated lactone (1a).This publication has 0 references indexed in Scilit: