title: Enantioselective synthesis of spiroacetals via silver(I)-promoted alkylation of hemiacetals: total synthesis of cephalosporolides E and F.
abstract: A silver(I)-promoted intramolecular hemiacetal alkylation has been developed that converts readily available keto-chlorodiols into functionalized spiroacetals containing 5,5-, 5,6-, and 5,7-membered ring systems. The efficiency of this process is demonstrated in a concise total synthesis of the fungal metabolites cephalosporolides E and F.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
authors.forename: Stanley
authors.initials: S
authors.lastname: Chang
authors.forename: Robert
authors.initials: R
authors.lastname: Britton
mesh_terms: D000164:Acremonium / Q000737:chemistry; D000478:Alkylation; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007202:Indicators and Reagents; D013141:Spiro Compounds; C540295:cephalosporolide E; C540296:cephalosporolide F; D012834:Silver