Related Experiment Video
Updated: Jul 16, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Integrated Chemoenzymatic Synthesis of Dolabellane-Type Diterpenes
Eigo Fukuda1, Seiya Endo1, Hiyuma Kurosaki1
1Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
None:
Stereoselective syntheses of four dolabellane-type diterpenes, 3,7,12-dolabellatriene, ent-dolabeserpenoic acid A, 3,7,18-dolabellatriene, and 3,4-epoxy-7,18-dolabelladiene were achieved. The syntheses feature chemoenzymatic cyclization of unnatural substrates using a diterpene cyclase, CotB2. Three unnatural substrates bearing synthetically useful functional groups, such as vinyl halide or ketone moieties, were designed based on the biosynthetic reaction mechanism of CotB2. CotB2-mediated cyclization of these unnatural substrates uniformly afforded 5/11-fused carbocycles bearing a vinyl halide or ketone moiety. C1-homologation of the resulting cyclic products delivered the target natural products in an optically active form. The cyclization reaction mechanism is proposed based on DFT calculations of the cation reaction pathways.
More Related Videos
08:51Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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...