Total synthesis of (+)-tedanolide.
A convergent, stereocontrolled total synthesis of (+)-tedanolide (1), an architecturally complex marine antitumor macrolide, has been achieved in 31 steps (longest linear sequence). Highlights of the synthesis comprise a highly efficient dithiane union, followed by an Evans-Tishchenko "oxidation" to enable formation of the seco-ester in the presence of an oxidatively labile dithiane, a highly refined protecting group strategy, and a chemo- and stereoselective epoxidation at C(18,19).
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. smithab@sas.upenn.edu
Lee
Dongjoo
D
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D007783:Lactones; D018942:Macrolides; C119775:tedanolide