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Journal article
A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A
Organic letters, Vol.24(36), pp.6499-6504
09/16/2022
PMCID: PMC10559756
PMID: 35944279
Web of Science ID: WOS:000841457900001
Abstract
A stereoselective synthetic entry point to the 5-8-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.
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Details
- Title
- A Stereoselective Photoinduced Cycloisomerization Inspired by Ophiobolin A
- Publication Details
- Organic letters, Vol.24(36), pp.6499-6504
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 6
- Grant note
- R01-GM125926 / National Institutes of Health; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA Carnegie Mellon University (CMU) TG-CHE160006 / NSF XSEDE; National Science Foundation (NSF)
- Copyright
- © American Chemical Society
- Identifiers
- WOS:000841457900001; 99381856993006600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English