Total synthesis of (-)-deguelin via an iterative pyran-ring formation strategy.
Enantioselective synthesis of (-)-deguelin was accomplished via an iterative pyran-ring formation approach. The key features involve the anionic addition of a chromene unit to aryloxy alkyl aldehyde for the double cyclization precursor and iterative pyran ring formation by Pd-catalyzed O-arylation and C-arylation, respectively.
Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Republic of Korea. ygsuh@snu.ac.kr.
Seungbeom
S
Lee
Hongchan
H
An
Dong-Jo
DJ
Chang
Jaebong
J
Jang
Kyeojin
K
Kim
Jaehoon
J
Sim
Jeeyeon
J
Lee
Young-Ger
YG
Suh
D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry; D012402:Rotenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D011714:Pyrans; D012402:Rotenone; D010165:Palladium; C107676:deguelin