Studies toward Providencin: The Furanyl-Cyclobutanol Segment

Spohr, Simon M.; Fürstner, Alois

doi:10.1021/acs.orglett.3c00327

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Studies toward Providencin: The Furanyl-Cyclobutanol Segment

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Spohr, Simon M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Spohr, S. M., & Fürstner, A. (2023). Studies toward Providencin: The Furanyl-Cyclobutanol Segment. Organic Letters, 25(9), 1536-1540. doi:10.1021/acs.orglett.3c00327.

Cite as: https://hdl.handle.net/21.11116/0000-000C-CD92-8

Abstract

The furanocembranoid providencin remains an unconquered bastion, although the synthesis of 17-deoxyprovidencin─lacking a single −OH group─has been accomplished in the past. This paper describes a practical approach to a properly hydroxylated building block via an iridium-catalyzed photosensitized intramolecular [2 + 2] cycloaddition as the key step. While an attempt to convert this compound into providencin via RCAM failed, it might well be elaborated into the natural product by adopting the literature route.