10-Step, Gram-Scale Total Synthesis of (–)-Bipinnatin J

21 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A concise, scalable total synthesis of (–)-Bipinnatin J is disclosed. Commencing from inexpensive starting materials, this marine diterpenoid was fashioned through a highly convergent synthesis enabled by Ni-electrocatalytic decarboxylative cross–coupling (DCC) taking advantage of succinate as an ethylene 2-carbon bridge, a unique halogen dance-Zweifel sequence to rapidly access a trisubstituted furan, a Ni-mediated 1,6-conjugate addition, and an asymmetric proton transfer.

Keywords

total synthesis
electrochemistry

Supplementary materials

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Supporting Information
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Detailed experimental procedures, failed route summaries, and analytical data
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