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

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 and Jongkook Lee
Journal of organic chemistry, Vol.80(6), pp.3315-3320
20/03/2015
DOI: https://doi.org/10.1021/acs.joc.5b00046
PMID: 25723100

Abstract

Alkylation Amides - chemistry Molecular Structure Pyrans - chemical synthesis Pyrans - chemistry Stereoisomerism
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).

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