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Enantioselective construction of the ABCDE pentacyclic core of the Strychnos alkaloids

Abstract:

An efficient enantioselective 12-step synthesis of the ABCDE pentacyclic core of the Strychnos alkaloids is described. A key feature of this approach is an organocatalyzed enantioselective desymmetrization to generate the morphan core in high ee and dr. After palladium-catalyzed installation of the indole moiety, a subsequent 5-exo-trig dearomatizing atom transfer radical cyclization was developed to construct the C-ring. Following a series of functional group interconversions, the pentacycli...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.7b00669

Authors


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Institution:
University of Oxford
Oxford college:
Wadham College
Role:
Author
St. John's College, Oxford More from this funder
Merck Sharp and Dohme More from this funder
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
19
Issue:
7
Pages:
1894-1897
Publication date:
2017-03-30
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pmid:
28357866
Source identifiers:
688764
Language:
English
Pubs id:
pubs:688764
UUID:
uuid:8bef593f-d546-4ef4-ab6f-2204e51714af
Local pid:
pubs:688764
Deposit date:
2017-08-20

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