Enantioselective synthesis of macrocyclic propargylic alcohols by [2,3] Wittig ring contraction. Synthesis of (+)-aristolactone and cembranoid precursors

Article abstract of DOI:10.1021/ja00217a039

The use of chiral lithium amide bases to initiate enantioselective [2,3] Wittig rearrangements of allylic ethers was investigated. The 13-membered propargylic ether 1, a nonresolvable racemate, afforded the 10-membered propargylic alcohol SS2 in 60-80% ee