Related Experiment Video
Updated: Aug 13, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Total synthesis and absolute stereochemistry of plakortone D
Patricia Y Hayes1, William Kitching
1Department of Chemistry, The University of Queensland, Brisbane 4072, Australia.
Abstract:
The first total synthesis of plakortone D is described and thereby establishes the structure and absolute stereochemistry of the most biologically active member of the marine-derived plakortone family. The sterically congested bicyclic lactone core results from a Pd(II)-induced hydroxycyclization-carbonylation-lactonization sequence on an enediol whose chirality was installed by AD-technology. Attachment of the side chain, also constructed using AD-methodology, was achieved by using a modified Julia coupling. The described approach enables acquisition of other plakortones and analogues, in the correct (natural) stereochemical series.
More Related Videos
Related Concept Videos
Prochirality
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Directing and Steric Effects in Disubstituted Benzene Derivatives
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

