Synthesis of the Tetracyclic Structure of Batrachotoxin Enabled by Bridgehead Radical Coupling and Pd/Ni-Promoted Ullmann Reaction | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4217710

Reference Type

Journal Article

Title

Synthesis of the Tetracyclic Structure of Batrachotoxin Enabled by Bridgehead Radical Coupling and Pd/Ni-Promoted Ullmann Reaction

Author(s)

Sakata, K; Wang, Y; Urabe, D; Inoue, M

Year

2018

Is Peer Reviewed?

Journal

Organic Letters
ISSN: 1523-7060
EISSN: 1523-7052

Volume

Issue

Page Numbers

130-133

Language

English

PMID

29232148

DOI

10.1021/acs.orglett.7b03482

Web of Science Id

WOS:000419749700034

Abstract

The steroidal ABCD-ring system of the potent neurotoxin batrachotoxin was efficiently assembled in a convergent fashion. Bridgehead radical coupling between the simple AB-ring and D-ring fragments (3 and 4) formed the sterically congested linkage at the C9-oxygen-attached tetrasubstituted carbon. The C-ring was then cyclized by the Pd/Ni-promoted Ullmann reaction of the vinyl triflate and vinyl bromide of 19, giving rise to tetracyclic structure 1.