The Journal of Organic Chemistry

. alpha.-Amino acid derivatives as chiral educts for asymmetric products. Synthesis of sphingosine from. alpha.'-amino-. alpha.,. beta.-ynones

RH Boutin, H Rapoport

文献索引：Boutin, Raymond H.; Rapoport, Henry Journal of Organic Chemistry, 1986 , vol. 51, # 26 p. 5320 - 5327

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被引用次数: 86

摘要

The utility of d-amino-n,@-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 a, P-ynones. The first route is very short and high yielding, merely involving two selective reductions after synthesis of the appropriate a, P-ynone. The second route involves alkylation of a 0-unsubstituted ynone and illustrates the synthetic versatility ...