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Synthesis of the himandrine skeleton

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Date

2004

Authors

O'Connor, Patrick
Mander, Lewis
McLachlan, Matthew

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.

Description

Keywords

Keywords: alkaloid derivative; alkene derivative; himandrine; unclassified drug; amination; article; Birch reduction; chemical analysis; chemical modification; chemical structure; Curtius rearrangement; cycloaddition; Diels Alder reaction; Galbulimima belgraveana;

Citation

URI

http://hdl.handle.net/1885/78442

Collections

ANU Research Publications

Source

Organic Letters

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/ol036308n

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