ArticleThe Journal of organic chemistry2018
Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Heck Macrocyclization in Forging Non-Natural Large Rings including Macrocyclic Drugs.International journal of molecular sciences · 2023Review
- Site-directed late-stage diversification of macrocyclic nannocystins facilitating anticancer SAR and mode of action studies.RSC medicinal chemistry · 2023Article
- Article
- The Tetrahydrofuran Motif in Polyketide Marine Drugs.Marine drugs · 2022Review
- Marine Natural Products from Tunicates and Their Associated Microbes.Marine drugs · 2021Review
- Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey-Seebach Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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7 authors.
Funding
Abstract
The mandelalides comprise a family of structurally complex marine macrolides that display significant cytotoxicity against several human cancer cell lines. Presented here is a full account on the development of an Anion Relay Chemistry (ARC) strategy for the total synthesis of (-)-mandelalides A and L, the two most potent members of the mandelalide family. The design and implementation of a three-component type II ARC/cross-coupling protocol and a four-component type I ARC union permits rapid access respectively to the key tetrahydrofuran and tetrahydropyran structural motifs of these natural products. Other highlights of the synthesis include an osmium-catalyzed oxidative cyclization of an allylic 1,3-diol, a mild Yamaguchi esterification to unite the northern and southern hemispheres, and a late-stage Heck macrocyclization. Synthetic mandelalides A and L displayed potent cytotoxicity against human HeLa cervical cancer cells (EC
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