title: Diastereoselective total synthesis of (+)-13-stemarene by fourth generation methods: a formal total synthesis of (+)-18-deoxystemarin.
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.
authors: Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, P.le Aldo Moro, 5, I-00185 Roma, Italy.
authors: Francesca
authors: F
authors: Leonelli
authors: Federico
authors: F
authors: Blesi
authors: Paolo
authors: P
authors: Dirito
authors: Andrea
authors: A
authors: Trombetta
authors: Francesca
authors: F
authors: Ceccacci
authors: Angela
authors: A
authors: La Bella
authors: Luisa M
authors: LM
authors: Migneco
authors: Rinaldo
authors: R
authors: Marini Bettolo
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C568415:(+)-13-stemarene; C568416:(+)-18-deoxystemarin; D004224:Diterpenes