Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 12, Pages 5042-5060Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200740b
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Funding
- National Science Foundation (X-ray Crystallographic facility) [CHE 0808983, CHE 0131112]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0808983] Funding Source: National Science Foundation
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Exploratory oxidative cyclization studies on cyclo-pentanelated and cyclohexenelated oroidin derivatives utilized Pummerer chemistry to generate pentacyclic structures related to the palau'amine family of sponge metabolites. Stereochemical issues were paramount, and appropriate choice of annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity for all of the core bonds.
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