A unified approach to the tedanolides: total synthesis of (+)-13-deoxytedanolide.
A unified approach for the construction of the potent marine antitumor agents (+)-tedanolide (1) and (+)-13-deoxytedanolide (2) is described. Highlights of the synthetic strategy include the development of a versatile bifunctional dithiane-vinyl iodide linchpin, the unorthodox use of the Evans-Tishchenko reaction, and a late-stage high-risk stereocontrolled introduction of the C(18,19) epoxide to achieve a total synthesis of (+)-13-deoxytedanolide (2).
Smith
Amos B
AB
Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Adams
Christopher M
CM
Barbosa
Stephanie A Lodise
SA
Degnan
Andrew P
AP
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
C409106:13-deoxytedanolide; D000970:Antineoplastic Agents; D007783:Lactones; D018942:Macrolides; C119775:tedanolide