Related Experiment Video
Updated: Aug 12, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Total syntheses of bengamides B and E
F R Kinder1, S Wattanasin, R W Versace
1Oncology Department, Novartis Pharmaceuticals Corporation, 556 Morris Avenue, Summit, New Jersey 07901, USA. frederick.kinder@pharma.novartis.com
Abstract:
Total syntheses of the cytotoxic marine natural products bengamides B and E are described. Both bengamides are prepared via amide coupling of a protected polyhydroxylated lactone intermediate 9 with a suitably substituted aminocaprolactam intermediate. Lactone 9 is prepared in five steps from commercially available alpha-D-glucoheptonic gamma-lactone. The key reactions are a selective deprotection of a 1,2-acetonide in the presence of a 1,3-acetonide and an (E)-selective olefination of an unstable aldehyde using a gem-dichromium reagent. The bengamide B lactam intermediate 10 is prepared in seven steps from commercially available (5R)-5-hydroxy-L-lysine (12). The desired S-configuration at the gamma-OH lactam position is established using the Mitsunobu reaction.
Related Concept Videos
NMR Spectroscopy of Benzene Derivatives
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Production of Antibiotics
Production of Pharmaceuticals

