ArticleChemical science2020
Cyclodepsipeptide alveolaride C: total synthesis and structural assignment.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Exploring the Synthetic Potential of Horner-Wadsworth-Emmons Reaction Toward the Synthesis of Polyketide Based Natural Products: A Review.Topics in current chemistry (Cham) · 2025Review
- Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy.ACS medicinal chemistry letters · 2024Article
- Yamaguchi esterification: a key step toward the synthesis of natural products and their analogs-a review.Frontiers in chemistry · 2024Review
- Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review.Molecules (Basel, Switzerland) · 2023Review
- Total synthesis of the antibacterial polyketide natural product thailandamide lactone.Chemical science · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
First stereoselective total synthesis of naturally occurring bioactive cyclodepsipeptide alveolaride C has been achieved using a convergent approach. This synthetic study enabled us to establish unambiguously the stereochemistry of three unassigned chiral centres embedded in the nonpeptidic segment as well as revised the stereochemistry of the proposed β-phenylalanine counterpart of the molecule. The key strategic features of this synthesis include Sharpless asymmetric dihydroxylation for installing the vicinal diol moiety, Julia-Kocienski olefination for constructing the aliphatic side chain, the Shiina protocol for intermolecular esterification, amide coupling and macrolactamization for the ring formation.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.