Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry.
The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, meso-symmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings. [Structure: see text]
Keller
Valerie A
VA
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1396, USA.
Kim
Ikyon
I
Burke
Steven D
SD
D003517:Cyclopentanes; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010165:Palladium; D000095662:Polyether Polyketides
D003517:Cyclopentanes; D004988:Ethers, Cyclic; D018942:Macrolides; D010165:Palladium; C070519:halichondrin B; D000095662:Polyether Polyketides