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The synthesis of (-)-cis- and (-)-trans-crobarbatic acid

Abstract:
The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Stevenson, CA More by this author
Helliwell, M More by this author
Ladduwahetty, T More by this author
Journal:
TETRAHEDRON-ASYMMETRY
Volume:
10
Issue:
7
Pages:
1315-1322
Publication date:
1999-04-09
DOI:
ISSN:
0957-4166
URN:
uuid:378ba6ba-84ba-4314-983e-d6f8ec3d3dca
Source identifiers:
36983
Local pid:
pubs:36983
Language:
English

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