Formal synthesis of (-)-apicularen A.
[reaction: see text] A formal synthesis of (-)-apicularen A has been completed. The synthesis features a cyanohydrin acetonide coupling as a convergent approach to the C9-C18 segment and an intramolecular Diels-Alder addition sequence to create both the 10-membered macrocycle and the aromatic ring.
Graetz
Benjamin R
BR
Department of Chemistry, 516 Rowland Hall, University of California-Irvine, Irvine, California 92697-2025, USA.
Rychnovsky
Scott D
SD
D000096:Acetone / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry
D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009570:Nitriles; C117813:apicularen A; C430593:cyanohydrin; D000096:Acetone