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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.