Total synthesis of oidiodendrolides and related norditerpene dilactones from a common precursor: metabolites CJ-14,445, LL-Z1271gamma, oidiolactones A, B, C, and D, and nagilactone F.
An efficient, high-yielding strategy has been developed for the asymmetric total synthesis of seven norditerpenoid dilactones known for their diverse biological properties. The three key steps employed to obtain a tricyclic lactone intermediate involved a Morita-Baylis-Hillman reaction, the stereocontrolled construction of a gamma-lactone through bromolactonization, and an efficient catalytic Reformatsky-type reaction. Access to CJ-14,445, LL-Z1271gamma, oidiolactones A, B, C, and D, and nagilactone F was possible from a common intermediate. Structures and stereochemistry were determined by X-ray analysis.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec, H3C 3J7, Canada. stephen.hanessian@umontreal.ca
Boyer
Nicolas
N
Reddy
Gone Jayapal
GJ
Deschênes-Simard
Benoît
B
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism
D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; D007783:Lactones; D013729:Terpenes; C461901:oidiolactone C; C013363:LL-Z 1271alpha; C004552:nagilactone C