Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 2, Pages 1398-1420Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02700
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Funding
- NSF [CHE-1262040]
- NIH [AI-138139]
- UC Irvine Regents' Dissertation Fellowship
- NSF Graduate Fellowship
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This study provides a detailed account of the concise and highly stereoselective synthesis of (+)-7,20-diisocyanoadociane (DICA), a structurally complex isocyanoditerpene with potent antiplasmodial activity. The synthesis strategy involves the construction of unsaturated tricyclic precursors followed by stereocontrolled Birch reductions and a subsequent bay ring formation to generate the isocycloamphilectane core.
A full account of the development of a concise and highly stereoselective synthesis of (+)-7,20-diisocyanoadociane (DICA)-a structurally complex isocyanoditerpene with potent antiplasmodial activity-is described. The strategy that evolved relies on the rapid construction of unsaturated tricyclic precursors designed to undergo stereocontrolled Birch reductions and a subsequent bay ring formation to generate the isocycloamphilectane core. This report is divided into three sections: (1) a description of the initial strategy and the results that focused our efforts on a single route to the DICA core, (2) a discussion of the precise choreography needed to enable a first-generation formal synthesis of (+/-)-DICA, and (3) the execution of a 13-step second-generation synthesis of (+)-DICA that builds on important lessons learned from the first-generation effort.
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