Divergent Synthesis of 17-nor-Cephalotane Diterpenoids through Developed Ynol-diene Cyclization

24 April 2024, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The diversity of complex molecular structures of Cephalotaxus diterpenoids poses great challenges in uncovering the pharmaceutical potential of these natural products. As a subfamily of Cephalotaxus diterpenoids, 17-norcephalotane diterpenoids possess polycyclic frameworks with seven-membered A ring bearing different oxidation states. On the basis of a novel ynol-diene cyclization developed as a rapid access to tropone unit, the first divergent strategy to 17-nor-cephalotane diterpenoids has been successfully established. Combining with a bioinspired stereoselective dual hydrogenation, the divergent total synthesis of (+)-3-deoxyfortalpinoid F, (+)-harringtonolide, (−)-fortalpinoids M/N/P, and analog (−)-20-deoxocephinoid P have been achieved in 14-17 linear longest steps starting from commercially available materials.

Keywords

natural product
divergent synthesis
ynol-diene cyclization

Supplementary materials

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Supporting Information file for Divergent Synthesis of 17-nor-Cephalotane Diterpenoids through Developed Ynol-diene Cyclization
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