title: Stereocontrolled formal synthesis of (+/-)-platensimycin.
abstract: The caged structure of platensimycin, known as Nicolaou's key intermediate for total synthesis of platensimycin, was synthesized stereoselectively by using the following key steps: (i) diastereoselective Diels-Alder reaction between gamma-benzoyloxy enone and tert-butyldimethylsiloxydiene, (ii) formation of a dihydropyran ring by intramolecular catalytic oxypalladation, and (iii) transannular radical cyclization of monothioacetal with tributyltin hydride and AIBN.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. jimatsuo@p.kanazawa-u.ac.jp
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Matsuo
authors.forename: Kosuke
authors.initials: K
authors.lastname: Takeuchi
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Ishibashi
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D013237:Stereoisomerism
chemical_list: D062365:Aminobenzoates; D000813:Anilides; D000218:Adamantane; C510909:platensimycin