Synthesis of a cyclic isostere of α-methyl homoserine by a stereoselective acylation-alkylation sequence of a chiral γ-lactam.

Abstract:

:Starting from a chiral 4-hydroxymethyl pyrrolidin-2-one, an isostere of α-methyl homoserine tethered on a γ-lactam ring was prepared exploiting a stereoselective acylation-methylation sequence, followed by Curtius rearrangement, and structural assignment was confirmed by n.O.e. experiments. By reverting the sequence, the 3-carboxy-3-methyl derivative having the opposite configuration at C-3 was obtained with total stereoselection, but Curtius rearrangement invariably afforded only inseparable mixtures of decomposition products.

journal_name

Amino Acids

journal_title

Amino acids

authors

Civitavecchia A,Martelli G,Orena M,Rinaldi S

doi

10.1007/s00726-014-1671-9

subject

Has Abstract

pub_date

2014-04-01 00:00:00

pages

1097-103

issue

4

eissn

0939-4451

issn

1438-2199

journal_volume

46

pub_type

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