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Total Asymmetric Synthesis of a New 9,12‐Anhydroerythronolide Aglycone
Author(s) -
GerberLemaire Sandrine,
Ainge Simon W.,
Glanzmann Cécile,
Vogel Pierre
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200202)85:2<417::aid-hlca417>3.0.co;2-1
Subject(s) - chemistry , aglycone , stereocenter , antimicrobial , stereochemistry , combinatorial chemistry , total synthesis , enantioselective synthesis , organic chemistry , glycoside , catalysis
Two novel, potentially antimicrobial erythronolide aglycon analogs ((−)‐ 9 and (−)‐ 30 , respectively), which incorporate a large number of contiguous stereogenic centers, have been prepared by multistep synthesis from simple chirons. The chemistry presented demonstrates the power of the so‐called ‘naked sugars of the second generation' approach. As for the sporeamicins, our macrolides are 9,12‐anhydroerythronolides, yet presenting a higher degree of complexity due to additional functional groups.