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Enantioselective [4 + 2]-Annulation of Chiral Crotylsilanes: Application to the Synthesis of a C1−C22 Fragment of Leucascandrolide A

2003; American Chemical Society; Volume: 5; Issue: 21 Linguagem: Inglês

10.1021/ol035581m

1523-7060

Les A. Dakin, James S. Panek,

Chemical synthesis and alkaloids

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.