An Intramolecular Para-phenolic Allylation Free Radical Cyclization Strategy for the Synthesis of Alkaloids and Terpenes with Spiro[4.5] Decane Architectures

Authors

Matthew G. Donahue, University of Southern MississippiFollow
Nicholas G. Jentsch, University of Southern Mississippi
Erin C. Realini, University of Southern Mississippi

Document Type

Article

Publication Date

8-2017

Department

Chemistry and Biochemistry

Abstract

A Tsuji-Trost variant of the Winstein-Masamune reaction has been investigated for the synthesis of the AC spirocyclic ring system 9 bearing a quaternary carbon found in the fawcettimine type Lycopodium alkaloids magellanine 1 and lycojaponicumin B 2 and cyclopiane diterpenes such as conidiogenone 3. Annulation of the B ring for the synthesis of tricyclic ABC cores was demonstrated utilizing a 5-exo-trig free radical cyclization of a primary carbon radical onto a cyclohexadienone generated with tri-n-butyl-germanium hydride (9 -> 11). (C) 2017 Elsevier Ltd. All rights reserved.

Publication Title

Tetrahedron Letters

Volume

58

Issue

33

First Page

3219

Last Page

3222

Recommended Citation

Donahue, M. G., Jentsch, N. G., Realini, E. C. (2017). An Intramolecular Para-phenolic Allylation Free Radical Cyclization Strategy for the Synthesis of Alkaloids and Terpenes with Spiro[4.5] Decane Architectures. Tetrahedron Letters, 58(33), 3219-3222.
Available at: https://aquila.usm.edu/fac_pubs/17628