Enantioselective total synthesis of (-)- and (+)-petrosin.
The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki-Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.
Toya
Hiroki
H
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
Okano
Kentaro
K
Takasu
Kiyosei
K
Ihara
Masataka
M
Takahashi
Atsushi
A
Tanaka
Haruo
H
Tokuyama
Hidetoshi
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D002384:Catalysis; D003500:Cyclization; D008386:Marine Biology; D015394:Molecular Structure; D047130:Petrosia / Q000737:chemistry; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D054837:Quinolizidines; C554883:petrosin