Hemisynthesis of new labdane derivatives from (-)-sclareol.
A straightforward and very simple access to different analogues of (+)-subersic acid 7, the unnatural enantiomer (compounds 12) from naturally occurring (-)-sclareol 1 is described. We also report new conditions for the preparation of keto-intermediate 8 using maleic acid and describe hemiketal 11 as the new intermediate of degradative oxidation of 1.
Fekih
Abdel Waheb
AW
Laboratoire de Chimie, Département des Sciences Fondamentales et Mixtes, Faculté de Médecine Dentaire, 5000 Monastir, Tunisia. fekihus@yahoo.com
Gafsi
Karima
K
Ferreiro-Mederos
Letitia
L
Hanquet
Gilles
G
D000818:Animals; D004224:Diterpenes / Q000737:chemistry*; D013058:Mass Spectrometry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D004224:Diterpenes; D013729:Terpenes; C497305:subersic acid; C070760:sclareol