title: Enantioselective [4 + 2]-annulation of chiral crotylsilanes: application to the synthesis of a C1-C22 fragment of leucascandrolide A.
abstract: [reaction: see text] The asymmetric synthesis of a C1-C22 fragment (2) of leucascandrolide A is described. Synthetic highlights include the construction of the C9-C22 pyran fragment using a formal [4 + 2]-annulation of a chiral organosilane. A diastereoselctive Mukaiyama aldol was used to introduce the C9 stereocenter and complete the assembly of the macrocycle's carbon skeleton.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Les A
authors.initials: LA
authors.lastname: Dakin
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D008956:Models, Chemical; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D012717:Sesquiterpenes; C408748:leucascandrolide A