Stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: total synthesis of (-)-centrolobine

Muhammad Latif; Jeong In Yun; Kalapati Seshadri; Hyoung Rae Kim; Chi Hoon Park; Haeil Park; Hyoungsu Kim; Jongkook Lee

doi:10.1021/acs.joc.5b00046

Stereoselective construction of 2,6-cis-disubstituted tetrahydropyrans via intramolecular amide enolate alkylation: total synthesis of (-)-centrolobine

J Org Chem. 2015 Mar 20;80(6):3315-20. doi: 10.1021/acs.joc.5b00046. Epub 2015 Mar 6.

Authors

Muhammad Latif^{1

2}, Jeong In Yun¹, Kalapati Seshadri³, Hyoung Rae Kim¹, Chi Hoon Park¹, Haeil Park³, Hyoungsu Kim⁴, Jongkook Lee^{1

3}

Affiliations

¹ †Bio-Organic Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea.
² ‡Korea University of Science and Technology, Daejeon 305-600, Republic of Korea.
³ §College of Pharmacy, Kangwon National University, 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 200-701, Republic of Korea.
⁴ ∥College of Pharmacy, Ajou University, Suwon, Gyeonggi-do 443-749, Republic of Korea.

PMID: 25723100
DOI: 10.1021/acs.joc.5b00046

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Amides / chemistry*
Molecular Structure
Pyrans / chemical synthesis
Pyrans / chemistry*
Stereoisomerism

Substances

Amides
Pyrans
centrolobin