Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 9, Pages 4783-4790Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00433
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Funding
- National Science Foundation [CHE-0611096]
- C. Eugene Bennett Department of Chemistry
- National Science Foundation-MRI program [CHE-1228366, CHE-1336071]
- Direct For Mathematical & Physical Scien [1336071] Funding Source: National Science Foundation
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1228336] Funding Source: National Science Foundation
- Division Of Chemistry [1336071] Funding Source: National Science Foundation
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An expedient synthesis corroborating the proposed structure of the tetracylic indole alkaloid ht-13-B is presented. Key synthetic steps include acyliminium ion allylation, a Mitsunobu reaction, a palladium-catalyzed Stille-Kelly cross coupling reaction, and a :carbon monoxide-mediated palladium-catalyzed reductive N-heterocyclization. The chiral centers are ultimately,derived from commercially available trans-4-hydroxy-L-proline.
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