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Epoxide opening-induced tandem 8-azabicyclo[3.2.1]octane to 6-azabicyclo[3.2.1]octane rearrangement-iminium allylation: synthesis of (+/-)-peduncularine.

Abstract:
An efficient Lewis acid induced nitrogen-driven rearrangement iminium-trapping cascade from an epoxytropinone 3 gives a 7-allylated 6-azabicyclo[3.2.1]octan-3-one 2, which is converted into the alkaloid (+/-)-peduncularine (1).
Publication status:
Published

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Publisher copy:
10.1021/ol100943j

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
12
Issue:
12
Pages:
2834-2837
Publication date:
2010-06-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:616f84ad-bd84-4d82-b8e0-33a5fad419c3
Source identifiers:
54763
Local pid:
pubs:54763

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