Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol

Naoto Hama; Toshihiro Aoki; Shohei Miwa; Miki Yamazaki; Takaaki Sato; Noritaka Chida

doi:10.1021/ol102856j

Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol

Org Lett. 2011 Feb 18;13(4):616-9. doi: 10.1021/ol102856j. Epub 2010 Dec 31.

Authors

Naoto Hama¹, Toshihiro Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Sato, Noritaka Chida

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 21194237
DOI: 10.1021/ol102856j

Abstract

A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Broussonetia / chemistry
Catalysis
Molecular Structure
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism
Tartrates / chemistry*

Substances

Alkaloids
Pyrrolidines
Tartrates
broussonetine F
diethyl tartrate