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A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements.

Abstract:
[reaction: see text] A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step.
Publication status:
Published

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Publisher copy:
10.1021/ol052333c

Authors


Luckhurst, CA More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
Organic letters
Volume:
7
Issue:
26
Pages:
5813-5816
Publication date:
2005-12-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:53f9a081-e492-4dd0-bfe1-1aff526138d7
Source identifiers:
52065
Local pid:
pubs:52065

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