Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5502-5505Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02473
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Funding
- Institute of General Medical Sciences of the U.S. Department of Health and Human Services [R01 GM65597, R35 GM127097]
- Gleysteen-Heisig summer fellowship
- University of Minnesota Undergraduate Research Opportunities Program
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A synthetic strategy formally equivalent to an intermolecular hexadehydro-Diels-Alder (HDDA) reaction is described. Sulfur-based linkers were designed and constructed by joining terminal alkynes or diynes using alkyne thiolate chemistry. The resulting tetraynes and triynes successfully underwent HDDA cyclization and benzyne trapping. Linker removal by reductive desulfurization was uneventful. The strategy was also found suitable for the tetradehydro-Diels Alder (TDDA) reaction.
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