Enantioselective Synthesis of Daurichromenic Acid and Confluentin

The first asymmetric synthesis of daurichromenic acid and confluentin is described. The key step of the sequence leading to both natural products is a highly enantioselectivedomino aldol/oxa Michael reaction (97 % ee) of farnesal and 2‐methoxy‐4‐methylsalicylaldehyde. The synthesis of daurichromenic...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010-02, Vol.2010 (6), p.1033-1036
Main Authors: Liu, Kegang, Woggon, Wolf-D.
Format: Article
Language:English
Subjects:
Aldol reactions
Chemistry
Chromenes
Domino reactions
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Michael reaction
Organic chemistry
Organocatalysis
Preparations and properties
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Summary:The first asymmetric synthesis of daurichromenic acid and confluentin is described. The key step of the sequence leading to both natural products is a highly enantioselectivedomino aldol/oxa Michael reaction (97 % ee) of farnesal and 2‐methoxy‐4‐methylsalicylaldehyde. The synthesis of daurichromenic acid and confluentin, two chromenes from Rhododendron dauricum, was achieved using a chiral lactol that was generated from farnesal and 2‐methoxy‐4‐methylsalicylaldehyde by an organocatalytic, highly enantioselective domino aldol/oxa Michael reaction.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200901403