A synthesis of the carbocyclic core of maoecrystal V.
An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
Kiel E
KE
Lazarski
Dennis X
DX
Hu
Charlotte L
CL
Stern
Regan J
RJ
Thomson
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; C545599:maoecrystal V