Related Experiment Video
Updated: May 23, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total synthesis of the proposed structure of aldingenin B
Michael T Crimmins1, Colin O Hughes
1Kenan, Caudill, Venable, and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
Abstract:
The first enantioselective total synthesis of the proposed structure of aldingenin B is reported in 16 steps from known compounds. The stereochemistry at C5 and C6 were established by an asymmetric acetal aldol. Following a ring-closing metathesis, a selective, substrate-controlled hydrogen bond-mediated dihydroxylation provided control of the C2 and C3 stereocenters. Discrepancies in the spectroscopic data of the synthetic and natural material led to the conclusion that the structure of the natural sample was misassigned.
More Related Videos
Related Concept Videos
Base-Catalyzed Aldol Addition Reaction
C–C Bond Formation: Aldol Condensation Overview
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Aldol Condensation vs Claisen Condensation

