Formal total synthesis of (+/-)-herbertene-1,13-diol and (+/-)-alpha-herbertenol via Ireland ester Claisen rearrangement and RCM reaction sequence

• Published in: Synlett no. 7; pp. 1173 - 1175
• Main Authors: Srikrishna, A, Lakshmi, BV
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 02.05.2005
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; OLEFIN METATHESIS; ENT-HERBERTANE CLASS; (+/-)-herbertene-1,13-diol; (+/-)-alpha-herbertenol; Ireland ester Claisen rearrangement; SESQUITERPENOIDS

A combination of Ireland ester Claisen rearrangement and ring-closing metathesis (RCM) reactions has been employed for efficient formal total syntheses of herbertene-1,13-diol and alpha-herbertenol, sesquiterpenes containing two vicinal quaternary carbon atoms on a cyclopentane ring.