Enantioselective [4 + 2]-annulation of chiral crotylsilanes: application to the synthesis of a C1-C22 fragment of leucascandrolide A.
[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.
Dakin
Les A
LA
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Panek
James S
JS
D008956:Models, Chemical; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D012717:Sesquiterpenes; C408748:leucascandrolide A