Total synthesis of grandisine D.
Total synthesis of grandisine D (5) was achieved by a Brønsted acid mediated Morita-Baylis-Hillman (MBH) ring-closure reaction and stereoselective aldol condensation with (S)-5-methylcyclohexenone (9) as key steps. The MBH approach was also applicable for the construction of the aza-fused bicyclic systems of pyrrolizidine and stemona alkaloids.
Kurasaki
Haruaki
H
Discovery Research Laboratories, Kyorin Pharmaceutical Co., Ltd., 2399-1, Nogi, Nogi-Machi, Shimotsuga-Gun, Tochigi 329-0114, Japan.
Okamoto
Iwao
I
Morita
Nobuyoshi
N
Tamura
Osamu
O
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure; D041901:Stemonaceae / Q000737:chemistry; D013237:Stereoisomerism
C551601:5-methylcyclohexenone; D000470:Alkaloids; D003512:Cyclohexanones; D007212:Indolizines; D008293:Malates; C546802:grandisine D; C030298:malic acid