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ChemInform Abstract: Use of an Electrocyclic Reaction of o-Quinodimethane and an Intramolecular Mannich-Type Cyclization in Diterpene Alkaloid Synthesis: A Synthesis of Nagata′s Intermediate for (.+-.)-Atisine.
First published: December 5, 1989
Abstract
The thermolysis of the benzocyclobutene (I) yields a Z-o-quinodimethane intermediate which undergoes an electrocyclic reaction to give the dihydronaphthalene (II).
ChemInform Abstract
The thermolysis of the benzocyclobutene (I) yields a Z-o-quinodimethane intermediate which undergoes an electrocyclic reaction to give the dihydronaphthalene (II). The latter is transformed to the title intermediate (XIIIa) via an intramolecular Mannich-type cyclization of the reduced compound (Xa). The epimer (XIIIb) is synthesized analogously and the structure of the precursor (XIIb) is confirmed by X-ray analysis (space group P1 with Z=4).
