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DOI: 10.1055/s-0028-1216728
Synthetic Efforts Towards the Synthesis of the Complex Diterpene Providencin
Publikationsverlauf
Publikationsdatum:
17. April 2009 (online)
Abstract
Providencin is a novel, highly oxygenated marine furanocembranolide featuring a cyclobutane ring and a highly strained 7,8-trans-epoxide. Various approaches to the total synthesis of this compound are reported. The cyclobutane moiety is generated via [2+2] cycloaddition and the furan ring is constructed via a Wipf palladium-catalyzed alkynone cyclization. The macrocyclic ring is closed via a Horner-Wadsworth-Emmons olefination or ring-closing metathesis. The latter reaction, however, produces the undesired 7,8-Z-olefin exclusively, and the conversion into the E-isomer has been, thus far, unsuccessful.
1 Introduction
2 Retrosynthetic Analysis
3 First Generation Approach
3.1 Synthesis of the Cyclobutane Moiety
3.2 Synthesis of the Western Fragment
3.3 Combination of Both Fragments and Ring Closure via
Horner-Wadsworth-Emmons
Olefination
4 Second Generation Approach via Ring-Closing Metathesis
5 Cyclobutane Model Studies
6 Conclusion
Key words
furanocembranolides - total synthesis - macrocycles, Horner-Wadsworth-Emmons olefination - ring-closing metathesis
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