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

doi:10.1021/acs.joc.5b00046

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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;
... Lee, Jongkook;
외 2명

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초록

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).

키워드

ENANTIOSELECTIVE TOTAL-SYNTHESIS; OXA-CONJUGATE CYCLIZATION; MAITLAND-JAPP REACTION; RING-CLOSURE REACTIONS; CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS; DIASTEREOSELECTIVE SYNTHESIS; PRINS CYCLIZATIONS; EFFICIENT APPROACH; CONCISE SYNTHESIS; MICHAEL REACTION

제목: Stereoselective Construction of 2,6-cis-Disubstituted Tetrahydropyrans via Intramolecular Amide Enolate Alkylation: Total Synthesis of (-)-Centrolobine

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

DOI: 10.1021/acs.joc.5b00046

발행일: 2015-03-20

유형: Article

저널명: The Journal of Organic Chemistry

권: 80

호: 6

페이지: 3315 ~ 3320