Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 3, Pages 919-926Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402082y
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Funding
- National Institutes of Health [GM 74776]
- Targeted Research Opportunity (TRO) Program of the Carol M. Baldwin Breast Cancer Fund (Stony Brook University)
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Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were obtained by the intermolecular radical cation Diels-Alder (RCDA) reaction. Each isomer was cleanly isolated without the aid of preparative HPLC. kingianins D, F, H, and J were prepared by way of these intermediates from commercially available materials in 10, 13, 9, and 17 steps, respectively. Kingianin A has already been prepared from one of these compounds. Completion of the synthesis of kingianin H relied on Manchand's one-step, three-carbon homologation.
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