Halichondrin B: synthesis of a C1-C14 model via desymmetrization of (+)-conduritol E.
[reaction: see text] A model C1-C14 segment (1) of halichondrin B was synthesized from (+)-conduritol E (7) in 18 steps and 2.9% overall yield. Key features of the synthesis include the novel ozonolytic desymmetrization of C(2)-symmetric diol 6, the early-stage construction of the C-ring which accompanies installation of the crucial C12 stereocenter, and the use of an enol ether C14-ketone surrogate as a precursor to the CDE-"caged" ketal.
Lambert
William T
WT
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
Burke
Steven D
SD
D000447:Aldehydes / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D012821:Silanes; D000095662:Polyether Polyketides
D000447:Aldehydes; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D018942:Macrolides; D012821:Silanes; C475532:conduritol E; C070519:halichondrin B; D000095662:Polyether Polyketides