Facile syntheses of (+)-gabosines A, D, and E.
(+)-Gabosines A (12), D (4), and E (5), which share the same trihydroxycyclohexenone skeleton, were synthesized from enone 11 as the common intermediate. The key building block 11 was accessed by an intramolecular aldol cyclization of a diketone derived from D-glucose (8).
Shing
Tony K M
TK
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin NT, Hong Kong, China. tonyshing@cuhk.edu.hk
Cheng
Hau M
HM
D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry; D007659:Ketones / Q000737:chemistry
D003512:Cyclohexanones; D007659:Ketones; C547936:gabosine A; C547937:gabosine D; C547938:gabosine E; D005947:Glucose