Novel domino reactions for diterpene synthesis.
New types of concerted domino acylation-cycloalkylation/alkylation-cycloacylation reactions have been described. These processes promoted by methanesulfonic acid-phosphorus pentoxide and concentrated H(2)SO(4), respectively, provide efficient, elegant, and expeditious routes for biologically active naturally occurring diterpenoids, namely (+/-)-ferruginol (1), (+/-)-nimbidiol (2), (+/-)-nimbiol (3), (+/-)-totarol (4), and ar-abietatriene (5).
Bhar
Shanta S
SS
Department of Chemistry, University of Mumbai, Mumbai-400098, India. b_shanta@yahoo.com
Ramana
M M V
MM
D045784:Abietanes; D000215:Acylation; D000478:Alkylation; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
C496113:1-phenylcyclopropene; D045784:Abietanes; D003521:Cyclopropanes; D004224:Diterpenes; C496110:ar-abietatriene; C431074:ferruginol; C496111:nimbidiol; C078548:totarol; C496109:nimbiol