In:
Angewandte Chemie, Wiley, Vol. 129, No. 23 ( 2017-06), p. 6709-6712
Abstract:
Described herein is the enantioselective syntheses of (+)‐ and (−)‐rishirilide B from the corresponding optically active β‐substituted tetralones, which were obtained by oxidative kinetic resolution based on α‐hydroxylation in the presence of a chiral guanidine‐bisurea bifunctional organocatalyst. Benzylic oxidation of the tetralones at C1 followed by regioselective isomerization of the oxabenzonorbornadiene structure led to rishirilide B. Our findings lead to the revision of the previously proposed (2R,3R,4R) absolute configuration of (+)‐rishirilide B to (2S,3S,4S).
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v129.23
DOI:
10.1002/ange.201701431
Language:
English
Publisher:
Wiley
Publication Date:
2017
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505868-5
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506609-8
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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