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Liposidomycins − Synthetic Studies Towards the Ribosyldiazepanone Moiety
Author(s) -
GravierPelletier Christine,
Milla Maria,
Merrer Yves Le,
Depezay JeanClaude
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:16<3089::aid-ejoc3089>3.0.co;2-l
Subject(s) - enantiopure drug , chemistry , moiety , epoxide , nucleoside , nucleophile , stereochemistry , ascorbic acid , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , food science
A synthesis of the enantiopure 2‐ribosyl‐1,4‐diazepan‐3‐one core of liposidomycins, a class of complex lipid nucleoside antibiotics, according to a flexible asymmetric synthesis strategy is described. It involves two building blocks, an enantiopure α‐azido‐β,γ‐epoxybutanol readily available from L ‐ascorbic acid, and an α‐ribosylamino acid obtained from D ‐ribose. Subsequent cyclization by regiospecific nucleophilic opening of the epoxide by the amino acid followed by peptidic coupling affords the target ribosyl diazepanone.