The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.

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Autori principali: Du, Lei, Dian, Longyang, Newmister, Sean A, Xia, Yuwei, Luo, Guanzhong, Sherman, David H, Li, Shengying
Natura: Artículo científico
Lingua:en
Pubblicazione: Chemical reviews 2025
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author Du, Lei
Dian, Longyang
Newmister, Sean A
Xia, Yuwei
Luo, Guanzhong
Sherman, David H
Li, Shengying
author_facet Du, Lei
Dian, Longyang
Newmister, Sean A
Xia, Yuwei
Luo, Guanzhong
Sherman, David H
Li, Shengying
Du, Lei
Dian, Longyang
Newmister, Sean A
Xia, Yuwei
Luo, Guanzhong
Sherman, David H
Li, Shengying
collection PubMed - marine biology
contents The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids. Du, Lei Dian, Longyang Newmister, Sean A Xia, Yuwei Luo, Guanzhong Sherman, David H Li, Shengying Indole Alkaloids Fungi Biological Products 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] -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.
format Artículo científico
id pubmed_39927617
institution PubMed
language en
publishDate 2025
publisher Chemical reviews
record_format pubmed
spellingShingle The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.
Du, Lei
Dian, Longyang
Newmister, Sean A
Xia, Yuwei
Luo, Guanzhong
Sherman, David H
Li, Shengying
Indole Alkaloids
Fungi
Biological Products
The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids. Du, Lei Dian, Longyang Newmister, Sean A Xia, Yuwei Luo, Guanzhong Sherman, David H Li, Shengying Indole Alkaloids Fungi Biological Products 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] -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.
title The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.
topic Indole Alkaloids
Fungi
Biological Products
url https://pubmed.ncbi.nlm.nih.gov/39927617/