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Stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: total synthesis of (-)-centrolobine.
Latif, Muhammad; Yun, Jeong In; Seshadri, Kalapati; Kim, Hyoung Rae; Park, Chi Hoon; Park, Haeil; Kim, Hyoungsu; Lee, Jongkook.
Afiliação
  • Latif M; †Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
  • Yun JI; ‡Korea University of Science and Technology, Daejeon 305-600, Republic of Korea.
  • Seshadri K; †Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
  • Kim HR; §College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
  • Park CH; †Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
  • Park H; †Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
  • Kim H; §College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
  • Lee J; ∥College of Pharmacy, Ajou University, Suwon, Gyeonggi-do 443-749, Republic of Korea.
J Org Chem ; 80(6): 3315-20, 2015 Mar 20.
Article em En | MEDLINE | ID: mdl-25723100
ABSTRACT
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).
Assuntos

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piranos / Amidas Idioma: En Ano de publicação: 2015 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piranos / Amidas Idioma: En Ano de publicação: 2015 Tipo de documento: Article