Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 20, Pages 7096-7109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo026287v
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- NIGMS NIH HHS [GM 37681] Funding Source: Medline
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The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium. salt --> alkylidenecarbene --> cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.
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