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Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor

Author:
Huang, Wen-Yu, Nishikawa, Toshio, Nakazaki, Atsuo
Source:
Journal of organic chemistry 2018 v.83 no.18 pp. 11108-11117
ISSN:
1520-6904
Subject:
Lycopodium alkaloids, chemical reactions, chemical structure, stereoselective synthesis, stereoselectivity
Abstract:
The stereocontrolled synthesis of a new azaspirocycle precursor of the fawcettimine-type Lycopodium alkaloids is described. Our approach provides an efficient entry to the azaspirocycle via a cascade Wacker-allylation sequence followed by a highly stereoselective Claisen rearrangement. This azaspirocycle, bearing all of the requisite functionality with pivotal stereogenic centers, is considered to be a versatile precursor useful for the fawcettimine-type Lycopodium alkaloids.
Agid:
6146212