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.

Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin / Leonelli, Francesca; Federico, Blesi; Paolo, Dirito; Andrea, Trombetta; Ceccacci, Francesca; LA BELLA, Angela; Migneco, Luisa Maria; MARINI BETTOLO, Rinaldo. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 76:16(2011), pp. 6871-6876. [10.1021/jo200945s]

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

LEONELLI, Francesca;CECCACCI, FRANCESCA;LA BELLA, ANGELA;MIGNECO, Luisa Maria;MARINI BETTOLO, Rinaldo
2011

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.
2011
(+)-13-stemarene, (+)-18-deoxystemarin, (+)-stemar-13-en-15-one 28
01 Pubblicazione su rivista::01a Articolo in rivista
Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin / Leonelli, Francesca; Federico, Blesi; Paolo, Dirito; Andrea, Trombetta; Ceccacci, Francesca; LA BELLA, Angela; Migneco, Luisa Maria; MARINI BETTOLO, Rinaldo. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 76:16(2011), pp. 6871-6876. [10.1021/jo200945s]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/388435
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