Germacrene B – a central intermediate in sesquiterpene biosynthesis

Abstract
Germacranes are important intermediates in the biosynthesis of eudesmane and guaiane sesquiterpenes. After their initial formation from farnesyl diphosphate, these neutral intermediates can become reprotonated for a second cyclisation to reach the bicyclic eudesmane and guaiane skeletons. This review summarises the accumulated knowledge on eudesmane and guaiane sesquiterpene hydrocarbons and alcohols that potentially arise from the achiral sesquiterpene hydrocarbon germacrene B. Not only compounds isolated from natural sources, but also synthetic compounds are dicussed, with the aim to give a rationale for the structural assignment for each compound. A total number of 64 compounds is presented, with 131 cited references.

Beilstein J. Org. Chem. 2023, 19, 186–203. doi:10.3762/bjoc.19.18

Source: Beilstein Journal of Organic Chemistry - February 20, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: biosynthesis configuration determination germacrene B structure elucidation terpenes Review Source Type: research