Synthetic approach toward the total synthesis of kempane diterpenes via transannular Diels-Alder strategy.
Total syntheses of two new (+/-)-kempane derivatives 30 and 47 were achieved with transannular Diels-Alder reaction (TADA) serving as the key step for the stereoselective formation of tricyclic [6.6.5] system 3. This synthetic approach also reveals that the geometry of the C3 group of such a tricyclic system plays an important role for the formation of the seven-membered kempane skeleton.
Caussanel
Franck
F
Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
Wang
Keyan
K
Ramachandran
Sreekanth A
SA
Deslongchamps
Pierre
P
D000818:Animals; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D020049:Isoptera / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure
D004224:Diterpenes; D047028:Macrocyclic Compounds