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

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).

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Veröffentlicht in:Journal of organic chemistry 2015-03, Vol.80 (6), p.3315-3320
Hauptverfasser: Latif, Muhammad, Yun, Jeong In, Seshadri, Kalapati, Kim, Hyoung Rae, Park, Chi Hoon, Park, Haeil, Kim, Hyoungsu, Lee, Jongkook
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Amides - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
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Zusammenfassung: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00046