High Stereochemical Diversity and Applications for the Synthesis of Marine Natural Products: A Library of Carbohydrate Mimics and Polyketide Segments

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 tetr...

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Bibliographic Details
Published in:Chemistry : a European journal 2000-09, Vol.6 (18), p.3313-3320
Main Authors: Misske, Andrea M., Hoffmann, H. Martin R.
Format: Article
Language:English
Subjects:
aldol reactions
biodiversity
carbohydrate
combinatorial chemistry
polyketides
Online Access:Get full text
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Summary: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.
ISSN:0947-6539
1521-3765
DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0