Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 33, Pages 11349-11352Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06823
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Funding
- National Institutes of Health [NIGMS RO1 086374]
- German Academic Exchange Service (DAAD)
- NIH Shared Instrument Grant [S10-RR027172]
- Office of Science, of the US Department of Energy [DE-AC02-05CH11231]
- NSF [CHE-0130862, CHE 82-08992, CHE 9633007]
- NIH [1S10RR016634-01, RR 02424A-01, SRR023679A]
- Grants-in-Aid for Scientific Research [17K08210] Funding Source: KAKEN
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Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the a-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the ent-3,4-secoatisane diterpenoid (-)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels Alder cycloaddition with ethylene gas (to construct the bicydo[2.2.2] octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of ent-3,4-seco-abietane diterpenoids using an intramolecular oxidative dearomatization.
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