The cycloaddition strategy for the synthesis of natural products containing carbocyclic seven-membered rings.
Highly substituted carbocyclic seven-membered rings are frequently found in natural products and their synthesis represents a significant challenge to the synthetic chemist. Direct intramolecular cyclization of these systems often proves difficult and this fact has catalyzed the development of a variety of strategies based on a convergent intermolecular cycloaddition strategy. This concept article discusses the major cycloaddition approaches utilized to access these types of structures and primarily focuses on examples employed in the synthesis of natural products.
Battiste
Merle A
MA
Department of Chemistry, University of Florida, Gainesville, FL 32611, USA.
Pelphrey
Phillip M
PM
Wright
Dennis L
DL
D001671:Biochemistry / Q000379:methods*; D001688:Biological Products / Q000138:chemical synthesis*; D054713:Bryostatins; D003078:Colchicine / Q000138:chemical synthesis; D003521:Cyclopropanes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis; D012717:Sesquiterpenes / Q000138:chemical synthesis
D001688:Biological Products; D054713:Bryostatins; D003521:Cyclopropanes; D004224:Diterpenes; D006576:Heterocyclic Compounds, 4 or More Rings; D018942:Macrolides; D012717:Sesquiterpenes; C409194:guanacastepene; C473358:sterpurene; C046785:bryostatin 1; C021985:cyclopropene; D003078:Colchicine