ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Total Synthesis of (+)-Disorazole Z1.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- Development of a Stereoselective Synthesis of Isomers of (+)-Disorazole Z1's Lateral Chain.The Journal of organic chemistry · 2025Article
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Authors and funding
4 authors.
Funding
Abstract
We wish to report the first total synthesis of (+)-disorazole Z1, a biologically extremely potent natural product (picomolar cytotoxicity) with complex molecular architecture featuring a 26-membered macrodiolide with lateral chains including a quaternary chiral carbon center. The complex acyclic lateral chains containing a stereochemical triad with the quaternary center surrounded by two hindered secondary alcohols were synthesized in a straightforward way by the use of two consecutive and highly diastereoselective aldol reactions with a lactone intermediate and further transformations to yield the desired (Z)-vinyl iodide. Successful esterification with a functionalized diene-stannane yielded the fully elaborated carbon skeleton. Making use of the C2 symmetry of the natural product, a double Stille coupling gave the protected natural product. Final deprotection provided (+)-disorazole Z1, which was fully identical to a natural sample.
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