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Updated: Jul 3, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Structure revision and synthesis of a novel labdane diterpenoid from Zingiber ottensii
John Boukouvalas1, Jian-Xin Wang
1Département de Chimie, Université Laval, Quebec City, Quebec G1K 7P4, Canada. john.boukouvalas@chm.ulaval.ca
Abstract:
The structure of ottensinin, a recently reported constituent of the medicinal plant Zingiber ottensii, was revised by re-evaluation of available NMR data from alpha-ylidenebutenolide 1 to gamma-pyrone 2, whose rearranged labdane skeleton is unprecedented. Structure 2 was proven by synthesis from (+)-sclareolide (nine steps, 27% overall yield) and was further validated by X-ray diffraction analysis of our synthetic sample. A plausible biosynthesis of 2 is proposed.
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Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
