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(-)-(2S,3R,Z)-Nakinadine A: first asymmetric synthesis and absolute configuration assignment.

Abstract:

Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3'-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (-)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (-)-(2S,3R,Z)-Nakinadine A was prepared...

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Publication status:
Published

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Publisher copy:
10.1021/ol500096r

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Inorganic Chemistry
Role:
Author
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Journal:
Organic letters
Volume:
16
Issue:
5
Pages:
1354-1357
Publication date:
2014-03-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:bb7262bb-a230-4270-8990-1f30c3fbf645
Source identifiers:
450903
Local pid:
pubs:450903

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