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Highly Diastereoselective Intramolecular [1,2]‐Stevens Rearrangements—Asymmetric Syntheses of Functionalized Isopavines as Morphinomimetics
Author(s) -
Hanessian Stephen,
Mauduit Marc
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011015)40:20<3810::aid-anie3810>3.0.co;2-8
Subject(s) - diastereomer , intramolecular force , stereochemistry , aryl , piperidine , chemistry , orientation (vector space) , mathematics , alkyl , organic chemistry , geometry
The power of visual imagery can reach Daliesque proportions in the mind's eye of the synthetic chemist. The topologically interesting isopavine nucleus, with an orthogonal orientation of two aryl groups, can be obtained as two diastereomeric structures, depending on the course of a [1,2]‐Stevens rearrangement. When viewed as a constrained piperidine, a close spatial relationship with morphine ( 1 ) becomes apparent. Indeed, tetracyclic isopavine 2 exhibits morphine‐like activity toward the human μ ‐opioid receptor.