Related Experiment Video
Updated: Aug 30, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Stereochemical elucidation of the 1,4 polyketide amphidinoketide I
Louise M Walsh1, Jonathan M Goodman
1Unilever Centre for Molecular Informatics, Department of Chemistry, Lensfield Road, Cambridge, UK CB2 1EW.
Abstract:
The relative and absolute stereochemistry of amphidinoketide I has been determined by the total synthesis of all the diastereoisomers. Molecular modelling suggests that the natural product is not the thermodynamically preferred diastereoisomer.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Aldol Condensation with β-Diesters: Knoevenagel Condensation
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...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

