Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6489-6493Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02286
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Funding
- National Science Foundation [CHE-1555300]
- NSF [CHE-0619339, CHE-0443618]
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A one-pot synthesis of dihydronaphthalenes and arylnaphthalenes from epoxides and common dipolarophiles is described. The reaction proceeds through photoredox activation of epoxides to carbonyl ylides, which undergo concerted [3 + 2] dipolar cycloaddition with dipolarophiles to provide tetrahydrofurans or 2,5-dihydrofurans. In the same flask, acid promoted rearrangement affords densely functionalized dihydronaphthalenes and arylnaphthalenes, respectively, in an overall redox-neutral sequence of transformations. Succinct total synthesis (4-6 steps) of pycnanthulignene B and C and justicidin E are reported.
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