Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family

Raquel Mato; Rubén Manzano; Efraím Reyes; Liher Prieto; Uxue Uria; Luisa Carrillo; Jose L. Vicario

doi:10.3390/catal12010067

Catalysts (Jan 2022)

Kinetic Resolution in Transannular Morita-Baylis-Hillman Reaction: An Approximation to the Synthesis of Sesquiterpenes from Guaiane Family

Raquel Mato,
Rubén Manzano,
Efraím Reyes,
Liher Prieto,
Uxue Uria,
Luisa Carrillo,
Jose L. Vicario

Affiliations

Raquel Mato: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Rubén Manzano: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Efraím Reyes: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Liher Prieto: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Uxue Uria: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Luisa Carrillo: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain
Jose L. Vicario: Department of Organic and Inorganic Chemistry, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain

DOI: https://doi.org/10.3390/catal12010067
Journal volume & issue: Vol. 12, no. 1
p. 67

Abstract

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An approximation to the synthesis of several sesquiterpenes from the Guaiane family is described in which the core structure was obtained through a transannular Morita-Baylis-Hillman reaction performed under kinetic resolution. Several manipulations of the obtained MBH adduct have been carried out directed towards the total synthesis of γ-Gurjunene, to the formal synthesis of Clavukerin A, to the synthesis of a non-natural isomer of isoguaiane and to the synthesis of an advanced intermediate in the total synthesis of Palustrol.

Published in Catalysts

ISSN: 2073-4344 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Technology: Chemical technology; Science: Chemistry
Website: https://www.mdpi.com/journal/catalysts

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