Title

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

Document Type

Article

Publication Date

8-16-2017

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-butylgermanium hydride (9 → 11).

Publication Title

Tetrahedron Letters

Volume

58

Issue

33

First Page

3219

Last Page

3222

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