Synthesis of (3 RS,3a SR,8a SR)-3-phenyloctahydrocyclohepta[ b]pyrrol-4(1 H)-one via the aza-Cope–Mannich rearrangement

A convenient and scalable method for the preparation of (3 RS,3a SR,8a SR)-phenyloctahydrocyclohepta[ b]pyrrol-4(1 H)-one based on the aza-Cope–Mannich rearrangement is described. This approach allows us to synthesize the target compound in nine steps in a high overall yield (42%) with complete ster...

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Bibliographic Details
Published in:Tetrahedron 2011-11, Vol.67 (47), p.9214-9218
Main Authors: Belov, Dmitry S., Lukyanenko, Evgeny R., Kurkin, Alexander V., Yurovskaya, Marina A.
Format: Article
Language:English
Subjects:
Allyl protective group
Aza-Cope–Mannich
cis-Cyclohepta[ b]pyrrolidine
Multigram preparation
Natural-like compounds
Synthesis (chemistry)
Tetrahedrons
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Summary:A convenient and scalable method for the preparation of (3 RS,3a SR,8a SR)-phenyloctahydrocyclohepta[ b]pyrrol-4(1 H)-one based on the aza-Cope–Mannich rearrangement is described. This approach allows us to synthesize the target compound in nine steps in a high overall yield (42%) with complete stereocontrol and up to 100 g scale. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.09.047