[3,3]-Sigmatropic rearrangement mediated synthesis of chiral building blocks for the preparation of Gemini and its analogs

Abstract

A novel synthetic methodology for the preparation of Gemini vitamin D₃ analogs has been developed. Our procedure uses a key sigmatropic rearrangement which allows control over the C-20 stereochemistry, providing a versatile method to introduce novel side-chains to the vitamin D scaffold giving access to new analogs with potentially interesting biological properties.