α-Amino Acid Derivatives as Chiral Educts for Asymmetric Products. Synthesis of Shpingosine from α'-Amino-α,β-ynones

Article abstract of DOI:10.1021/jo00376a050

The utility of α'-amino-α,β-ynones in the chirospecific synthesis of sphingosine is demonstrated.Thus, a protected L-serine isoxazolidide has been converted to sphingosine by two routes, both via α,β-ynones.The first route is very short and high yielding, merely involving two selective reductions after synthesis the appropriate α,β-ynone.The second route involves alkylation of a β-unsubstituted ynone and illustrates the synthetic versatility of the α'-amino-α,β-ynone system.Further routes through conjugate 1,4-additions to ynones are demonstrated but are limited by the highly reactive nature of this system.