title: Synthesis of tedanolide and 13-deoxytedanolide. Assembly of a common C(1)-C(11) subtarget.
abstract: [formula: see text] In this Letter we describe a synthetic strategy and an efficient assembly of a common C(1)-C(11) subtarget, (-)-3, for (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), architecturally complex marine macrolides displaying potent antitumor activity. Key elements of the synthesis include two iterations of the Evans aldol protocol to construct the C(1)-C(6) moiety and a stereocontrolled vinyl anion addition to generate the C(8,9) trisubstituted olefin incorporating stereogenicity at C(7). Alkylation with a model epoxide demonstrates that (-)-3 is a competent dithiane for further elaboration of the macrolide skeleton.
authors.affiliation: Department of Chemistry, University of Pennsylvania, Philadelphia, USA. smithab@sas.upenn.edu
authors.forename: A B
authors.initials: AB
authors.lastname: Smith
authors.forename: S A
authors.initials: SA
authors.lastname: Lodise
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides / Q000138:chemical synthesis*
chemical_list: C409106:13-deoxytedanolide; D000903:Antibiotics, Antineoplastic; D007783:Lactones; D018942:Macrolides; C119775:tedanolide