An expedient enantioselective strategy for the oxatetracyclic core of platensimycin.
An enantioselective route for the synthesis of oxatetracyclic core of platensimycin is reported for the first time using a 5-exo-trig cyclization followed by intramolecular etherification as key reactions. The requisite dienynone for the radical cyclization is synthesized in eight steps from the Wieland-Miescher ketone employing a Claisen rearrangement.
Kaliappan
Krishna P
KP
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, India. kpk@chem.iitb.ac.in
Ravikumar
Velayutham
V
D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry*; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry*; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D008968:Molecular Conformation; D013237:Stereoisomerism
D062365:Aminobenzoates; D000813:Anilides; D000218:Adamantane; C510909:platensimycin