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A Combined Intramolecular Diels–Alder/Intramolecular Schmidt Reaction: Formal Synthesis of (±)‐Stenine
Author(s) -
Golden Jennifer E.,
Aubé Jeffrey
Publication year - 2002
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(20021115)41:22<4316::aid-anie4316>3.0.co;2-u
Subject(s) - intramolecular force , stereocenter , diels–alder reaction , chemistry , intramolecular reaction , formal synthesis , cascade reaction , stereochemistry , cascade , organic chemistry , enantioselective synthesis , catalysis , chromatography
Four stereocenters and three rings are established in one step in a new formal synthesis of (±)‐stenine (see scheme). This key reaction cascade consists of an intramolecular Diels–Alder reaction followed by an intramolecular Schmidt reaction. The resulting tricyclic intermediate was readily transformed into a known intermediate en route to stenine, thus completing the formal synthesis.