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American Chemical Society, Journal of Organic Chemistry, 16(76), p. 6871-6876, 2011

DOI: 10.1021/jo200945s

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Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin

Journal article published in 2011 by Francesca Leonelli, Federico Blesi, Paolo Dirito, Andrea Trombetta, Francesca Ceccacci ORCID, Angela La Bella, Luisa Maria Migneco, Rinaldo Marini Bettolo, Rinaldo Marini Bettolo
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

The problem of constructing diastereoselectively the C/D ring system of stemarane diterpenes from a bicyclo[2.2.2]octane intermediate was solved resulting in very simple synthesis of (+)-13-stemarene 1. The obtaining of the latter represents also a formal synthesis of (+)-18-deoxystemarin 2. In the key step, the epimeric mixture 10, dissolved in toluene, was converted by the action of TsOH into (+)-stemar-13-en-15-one 28.