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A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A.

ABSTRACT: A stereoselective synthetic entry point to the 5-8-5 carbocyclic core of the ophiobolins was developed. This strategy exploits the chiral tertiary alcohol of ophiobolin A to guide assmebly of the 5-8-5 scaffold in a single step via a photoinitiated cycloisomerization. Mechanistic insights into the origin of stereocontrol in this reaction are described, as are efforts to elaborate the resultant fused 5-8-5 ring system to the pharmacophore of ophiobolin A.

SUBMITTER: Law JA

PROVIDER: S-EPMC10559756 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A.

Law James A JA Callen Daniel P DP Paola Elena L EL Gomes Gabe G Frederich James H JH

Organic letters 20220809 36

A stereoselective synthetic entry point to the 5-8-5 carbocyclic core of the ophiobolins was developed. This strategy exploits the chiral tertiary alcohol of ophiobolin A to guide assmebly of the 5-8-5 scaffold in a single step via a photoinitiated cycloisomerization. Mechanistic insights into the origin of stereocontrol in this reaction are described, as are efforts to elaborate the resultant fused 5-8-5 ring system to the pharmacophore of ophiobolin A. ...[more]

PMID: 35944279

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