Sesquiterpenes are a structurally diverse class of compounds that have been isolated from a wide range of living organisms. Spirolepechinene is a member of the rare spirojatamane class of sesquiterpenes with a unique relative stereochemistry about its spirocentre. While the other two members of this class have been synthesized, the differences in stereochemistry renders these previously-reported methods not applicable to the synthesis of spirolepechinene. Herein we present an efficient method for the synthesis of the spirocyclic core of spirolepechinene that produces the required stereochemistry for this unique natural product with high diastereoselectivity

Duhamel, N.; Larcher, R.; Guella, G.; Pilkington, L.I.; Fedrizzi, B.; Barker, D. (2019). Stereoselective synthesis of the spirocyclic ring system of the sesquiterpene spirolepechinene. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 8 (4): 462-465. doi: 10.1002/ajoc.201900151 handle: http://hdl.handle.net/10449/58760

Stereoselective synthesis of the spirocyclic ring system of the sesquiterpene spirolepechinene

Larcher, Roberto;
2019-01-01

Abstract

Sesquiterpenes are a structurally diverse class of compounds that have been isolated from a wide range of living organisms. Spirolepechinene is a member of the rare spirojatamane class of sesquiterpenes with a unique relative stereochemistry about its spirocentre. While the other two members of this class have been synthesized, the differences in stereochemistry renders these previously-reported methods not applicable to the synthesis of spirolepechinene. Herein we present an efficient method for the synthesis of the spirocyclic core of spirolepechinene that produces the required stereochemistry for this unique natural product with high diastereoselectivity
Sesquiterpene
Stereoselective synthesis
Natural product
Spirojatamane
Spirocenter
Settore CHIM/01 - CHIMICA ANALITICA
2019
Duhamel, N.; Larcher, R.; Guella, G.; Pilkington, L.I.; Fedrizzi, B.; Barker, D. (2019). Stereoselective synthesis of the spirocyclic ring system of the sesquiterpene spirolepechinene. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 8 (4): 462-465. doi: 10.1002/ajoc.201900151 handle: http://hdl.handle.net/10449/58760
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