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Studies toward Providencin: The Furanyl-Cyclobutanol Segment.

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.

SUBMITTER: Spohr SM

PROVIDER: S-EPMC10012265 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Studies toward Providencin: The Furanyl-Cyclobutanol Segment.

Spohr Simon M SM Fürstner Alois A

Organic letters 20230227 9

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 lit ...[more]

PMID: 36847332

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