Studies on the synthesis of tedanolide. 2. Stereoselective synthesis of a protected C(1)-C(12) fragment.
[reaction: see text] Highly diastereoselective syntheses of diketo esters 6a and 6b are described. These intermediates undergo efficient aldol reactions with protected C(13)-C(21) aldehydes 3 and 23, thereby providing advanced C(1)-C(21) tedanolide seco ester precursors 9a and 9b.
Roush
William R
WR
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA. roush@umich.edu
Newcom
Jason S
JS
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000970:Antineoplastic Agents; D004952:Esters; D007783:Lactones; D018942:Macrolides; C119775:tedanolide