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Preparation of Intermediates for the Synthesis of Polycyclic Alkaloids: A New Access to the Azabicyclic Core of the Stemona Alkaloids
Author(s) -
Cid Pau,
Closa Montserrat,
de March Pedro,
Figueredo Marta,
Font Josep,
Sanfeliu Elena,
Soria Angeles
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400322
Subject(s) - chemistry , pyrrolidine , piperidine , cycloaddition , stereochemistry , decane , organic chemistry , catalysis
Several isoxazolidines, derived from the 1,3‐dipolar cycloaddition of α,β‐hexenolides to cyclic nitrones, were converted into the corresponding piperidine‐ and pyrrolidine‐oxepinones by reduction of the nitrogen−oxygen bond. The potential of the resulting amino alcohols as synthetic precursors of polycyclic alkaloids was explored. These intermediates provide a new access to the 1‐azabicyclo[5.3.0]decane core of the Stemona alkaloids. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)