Studies on the Asymmetric Synthesis of Pyrrolidine Alkaioids and Related Compounds(Ⅰ)──Synthesis or a Chiral Precursor for Preussin and AHPPA

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (12): 1914.

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Studies on the Asymmetric Synthesis of Pyrrolidine Alkaioids and Related Compounds(Ⅰ)──Synthesis or a Chiral Precursor for Preussin and AHPPA

HUANG Pei-Qiang, RUAN Yuan-Ping

Department of Chemistry, Xiamen University, Xiamen, 361005

Received:1995-02-09 Revised:1995-05-20 Online:1995-12-24 Published:1995-12-24

Abstract

Abstract: Starting from(S)-malic aicd, the stereoselective synthesis of(4S, 5R)-1,5-dibenzyl-4-benzyloxyl-2-pyrrolidone 9 by two methods was described.The key steps in the synthesis are two asymmetric α-amidoalkylation.The asymmetric α-amidoalkylation was easily achieved either from sulfone 7by Ley's method or from 5 via an addition-reduction proceed to provide 9 in good(4/1 for 7) to excellent(97/3 for 5)trans stereoselectivity.Compound 9 is a chiral precursor for(-)-preussin and(3S,4R )-4-amino-3-hydroxyl-5-phenylpentanoic acid(AHPPA).

Key words: Preussin, 4-Amino-3-hydroxyl-5-phenylpentanoic acid, Asymmetric synthesis, α-Amidoalkylation, 1,5-Dibenzyl-4-benzyloxyl-2-pyrrolidone

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HUANG Pei-Qiang, RUAN Yuan-Ping. Studies on the Asymmetric Synthesis of Pyrrolidine Alkaioids and Related Compounds(Ⅰ)──Synthesis or a Chiral Precursor for Preussin and AHPPA[J]. Chem. J. Chinese Universities, 1995, 16(12): 1914.

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Studies on the Asymmetric Synthesis of Pyrrolidine Alkaioids and Related Compounds(Ⅰ)──Synthesis or a Chiral Precursor for Preussin and AHPPA

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