Enantioselective Formation of Functionalized 1,3-Disubstituted Allenes: Synthesis of α-Allenic ω-Carbomethoxy Alcohols of High Optical Purity

Article abstract of DOI:10.1021/jo00003a033

A general, high yield synthesis of multigram quantities of the title allenic alcohols is described.Intermediate 5, derived from D-mannitol, was elaborated to both enantiomers (10 and 11) of the anitfungal constituent (11) of Sapium japonicum and the lower homoglogue (16) useful for synthesis of allenyl prostaglandins.The natural material was thus shown to possess the R configuration.The product allenes were formed in >94percent ee as determined by 13C NMR spectral analysis of the corresponding Mosher esters.