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Flexible strategy for the synthesis of pyrrolizidine alkaloids.

Abstract:

A general strategy for the production of pyrrolizidine alkaloids is described, starting from intermediate (+)-9. The key features are diastereoselective dihydroxylation, inversion at the ring junction by hydroboration of an enamine, and ring closure to form the bicyclo ring system. This route is attractive because of its brevity and versatility; four natural products were prepared with differing stereochemistry and substitution patterns. Finally, this work allowed assignment of the absolute s...

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Publication status:
Published

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Publisher copy:
10.1021/ol801415d

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Thomas, RE More by this author
Cheeseman, MD More by this author
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Journal:
Organic letters
Volume:
10
Issue:
16
Pages:
3615-3618
Publication date:
2008-08-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:7a14d44d-b706-457b-92ef-e4d355879bac
Source identifiers:
34318
Local pid:
pubs:34318

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