Synthesis of (E)-δ-hydroxy-β,γ-dehydroα-amino acids, a new class of vinylglycines by the rearrangement ofβ acetoxyallylglycine derivatives.

Abstract:

:The efficient synthesis ofδ-hydroxy-β,γ-dehydroα-amino acids (1) was achieved by the hybrid process, in which the Pd(II)-assisted rear-rangement ofβ-acetoxyallylglycine ester (6) afforded the corresponding (E)-δ-acetoxyvinylglycine derivatives (7) in a moderate yield. The chemo- and stereo-selective hydrolysis of7 was accomplished by the use of microbial lipase (Amano PS) to afford the allylic alcohol (8), which was transformed into1 in two step sequence.

journal_name

Amino Acids

journal_title

Amino acids

authors

Kirihata M,Fukuari M,Izukawa T,Ichimoto I

doi

10.1007/BF00807269

subject

Has Abstract

pub_date

1995-12-01 00:00:00

pages

317-25

issue

4

eissn

0939-4451

issn

1438-2199

journal_volume

9

pub_type

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