Advances Toward Amphidinolides C, F and U: Isolations, Synthetic Studies and Total Syntheses
Abstract: Amphidinolides C, F, and U, including C2‐C4 analogs, are highly cytotoxic marine macrolides, mainly isolated from dinoflagellates of the genus Amphidinium. All these polyketides share a 75 % or more similar structure, highlighted by a macrolactone ring, at least one trans‐2,5‐substituted‐THF motif and a characteristic polyenic side chain. From their isolation and absolute configurational assignment, the total synthesis of these marine macrolides represented an intense challenge to the organic synthesis community over the last 15 years, with around 14 research groups engaged in this inspiring task. In the first part of this review, we present the different approaches to the isolation and characterization of these natural products, including the most recent analogs, which may cast doubt on the biogenetic origin of these compounds. The various synthetic approaches to the total synthesis of C, F, and U amphidinolides are presented in a second part, focusing on key reactions and/or innovative strategies. The review concludes in a third section summarizing the successful approaches leading to the total synthesis of one of the members of this amphidinolide subfamily.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
Advances Toward Amphidinolides C, F and U: Isolations, Synthetic Studies and Total Syntheses ; day:11 ; month:03 ; year:2024 ; extent:43
Chemistry - a European journal ; (11.03.2024) (gesamt 43)
- Urheber
-
Ciss, Ismaila
Seck, Matar
Figadère, Bruno
Ferrié, Laurent
- DOI
-
10.1002/chem.202400471
- URN
-
urn:nbn:de:101:1-2024031213055928207384
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 11:01 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Ciss, Ismaila
- Seck, Matar
- Figadère, Bruno
- Ferrié, Laurent
Ähnliche Objekte (12)
Synthesis of C2-tritwistane, synthetic and theoretical studies toward polytwistane and syntheses of twistanamines as potentential antiviral agents
Total syntheses of surugamides and thioamycolamides toward understanding their biosynthesis
Recent Advances Towards Syntheses of Diterpenoid Alkaloids
Automation of Flow Syntheses by AI Synthetic Route Design and Implementation
Recent Advances in Phenol Dearomatization and Its Application in Complex Syntheses
Advances in synthetic chemistry
Studies toward the total syntheses of waixenicin A and jerantinine E
Recent advances in the syntheses of anthracene derivatives
Recent Advances in Synthetic Application and Engineering of Halogenases
Toward Synthetic Physical Fingerprint Targets
Toward Synthetic Physical Fingerprint Targets
Synthetic study toward tridachiapyrone B
Synthesis of C2-tritwistane, synthetic and theoretical studies toward polytwistane and syntheses of twistanamines as potentential antiviral agents
Total syntheses of surugamides and thioamycolamides toward understanding their biosynthesis
Recent Advances Towards Syntheses of Diterpenoid Alkaloids
Automation of Flow Syntheses by AI Synthetic Route Design and Implementation
Recent Advances in Phenol Dearomatization and Its Application in Complex Syntheses
Advances in synthetic chemistry
Studies toward the total syntheses of waixenicin A and jerantinine E
Recent advances in the syntheses of anthracene derivatives
Recent Advances in Synthetic Application and Engineering of Halogenases
Toward Synthetic Physical Fingerprint Targets
Toward Synthetic Physical Fingerprint Targets
Synthetic study toward tridachiapyrone B
Synthesis of C2-tritwistane, synthetic and theoretical studies toward polytwistane and syntheses of twistanamines as potentential antiviral agents
Total syntheses of surugamides and thioamycolamides toward understanding their biosynthesis
Recent Advances Towards Syntheses of Diterpenoid Alkaloids
Automation of Flow Syntheses by AI Synthetic Route Design and Implementation
Recent Advances in Phenol Dearomatization and Its Application in Complex Syntheses
Advances in synthetic chemistry
Studies toward the total syntheses of waixenicin A and jerantinine E
Recent advances in the syntheses of anthracene derivatives
Recent Advances in Synthetic Application and Engineering of Halogenases
Toward Synthetic Physical Fingerprint Targets
Toward Synthetic Physical Fingerprint Targets