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Enantioselective synthesis of the predominant AB ring system of the Schisandra nortriterpenoid natural products.

Abstract:
An enantioselective synthesis of the AB ring system common to the majority of the Schisandra nortriterpenoid natural products is reported. Key steps include a stereospecific ring opening of a trisubstituted epoxide and the use of a β-lactone to enable installation of the gem-dimethyl functionality of the B ring. An acetalization strategy played a key role in a late-stage biomimetic AB ring bicyclization.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/ol502027m

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Name:
Engineering and Physical Sciences Research Council
Grant:
EP/E055273/1
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Name:
German Academic Exchange Service
More from this funder
Name:
Agency for Science, Technology and Research
Publisher:
American Chemical Society
Journal:
Organic letters More from this journal
Volume:
16
Issue:
17
Pages:
4480-4483
Publication date:
2014-09-01
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Language:
English
Keywords:
Pubs id:
pubs:481507
UUID:
uuid:d4c8c607-1d31-472b-973f-c0c8b1742fd1
Local pid:
pubs:481507
Source identifiers:
481507
Deposit date:
2014-08-29

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