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

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

Organic letters (2011-01-05)
Naoto Hama, Toshihiro Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Sato, Noritaka Chida
PMID21194237
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.

MATERIALS
Product Number
Brand
Product Description
213969
Sigma-Aldrich
(−)-Diethyl D-tartrate, ≥99%
Pricing and availability is not currently available.
156841
Sigma-Aldrich
(+)-Diethyl L-tartrate, ≥99%
Pricing and availability is not currently available.
W237809
Sigma-Aldrich
Diethyl L-tartrate, ≥99%, FG
Pricing and availability is not currently available.