Stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: total synthesis of (-)-centrolobine.
A highly stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans was achieved by using an intramolecular amide enolate alkylation with KHMDS. The efficiency and practicality of this methodology was successfully demonstrated in the total synthesis of (-)-centrolobine (1).
†Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.|‡Korea University of Science and Technology, Daejeon 305-600, Republic of Korea.
Muhammad
M
Latif
†Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
Jeong In
JI
Yun
§College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
Kalapati
K
Seshadri
†Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
Hyoung Rae
HR
Kim
†Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
Chi Hoon
CH
Park
§College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
Haeil
H
Park
∥College of Pharmacy, Ajou University, Suwon, Gyeonggi-do 443-749, Republic of Korea.
Hyoungsu
H
Kim
†Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.|§College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
Jongkook
J
Lee
D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D011714:Pyrans; C432457:centrolobin