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High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments
Author(s) -
Misske Andrea M.,
Hoffmann H. Martin R.
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000915)6:18<3313::aid-chem3313>3.0.co;2-0
Subject(s) - enantiopure drug , anomer , polyketide , aldol reaction , stereochemistry , chemistry , natural product , carbohydrate , enantioselective synthesis , organic chemistry , biosynthesis , enzyme , catalysis
Abstract We have developed a powerful concept for the rapid assembly of a series of twenty‐four homochiral building blocks from simple racemic trans ‐2,4‐dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one. The series comprises eight stereochemical pentades of anomeric [3.3.1]lactone acetals, eight stereochemical tetrades of anomeric carbohydrate mimics, and eight stereotetrades of acyclic polypropionate units. The utility of these enantiopure materials (average 94 % ee ) in natural product synthesis is demonstrated and shown to complement the popular aldol method.