A divergent approach to the myriaporones and tedanolide: completion of the carbon skeleton of myriaporone 1.
[reaction: see text] A linear but concise synthetic approach toward the structurally related natural products myriaporone and tedanolide is reported. The route is highlighted by a stereoselective homoallenylboration and a regio- and chemoselective nitrile oxide cycloaddition. Installation of the (Z)-olefin completed the carbon skeleton of myriaporone 1.
Taylor
Richard E
RE
Department of Chemistry and Biochemistry and the Walther Cancer Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA. taylor.61@nd.edu
Hearn
Brian R
BR
Ciavarri
Jeffrey P
JP
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001896:Boron Compounds / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis; D009570:Nitriles / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D000970:Antineoplastic Agents; D001896:Boron Compounds; D004852:Epoxy Compounds; D007783:Lactones; D018942:Macrolides; D009570:Nitriles; C476087:myriaporone 1; C119775:tedanolide