The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids
Lei Du1, Longyang Dian1, Sean A Newmister2
1State Key Laboratory of Microbial Technology, Shandong University, Qingdao, Shandong 266237, China.
Abstract:
Fungal indole alkaloids bearing a bicyclo[2.2.2]diazaoctane (BCDO) core structure are a fascinating family of natural products that exhibit a wide spectrum of biological activities. These compounds also display remarkable structural diversity, with many different diastereomers and enantiomers produced by specific fungal strains. The biogenesis of the unique BCDO moiety has long been proposed to involve an intramolecular [4+2] hetero-Diels-Alder (IMDA) reaction, but the exact mechanisms for this hypothetical transformation have remained elusive until recently. This review aims to summarize the whole history of synthetic and biosynthetic studies of fungal BCDO indole alkaloids, by covering the discovery, biomimetic syntheses, total syntheses, biosynthetic pathway elucidation, and biological activities of representative compounds. We highlight the mutual inspiration and corroboration between biological and synthetic chemists in exploring the intriguing biosynthetic mysteries of this family of natural products. We also provide perspectives and clues for the remaining biosynthetic problems.
More Related Videos
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
