Total synthesis of (+)-ileabethoxazole via an iron-mediated Pauson-Khand [2 + 2 + 1] carbocyclization.
Studies describe the total synthesis of (+)-ileabethoxazole (1) using a Stille cross-coupling reaction of propargylic stannanes with 5-iodo-1,3-oxazoles to produce 1,1-disubstituted allenes (11). An iron-mediated [2 + 2 + 1] carbocyclization yields a novel cyclopentenone for elaboration to 1. Site-selective palladium insertion reactions allow for regiocontrolled substitutions of the heterocycle. Asymmetric copper hydride reductions are examined, and strategies for the formation of the central aromatic ring are discussed.
Department of Chemistry, Indiana University , Bloomington, Indiana 47405, United States.
David R
DR
Williams
Akshay A
AA
Shah
D000466:Alkadienes / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000466:Alkadienes; D003517:Cyclopentanes; D010080:Oxazoles; C000597489:ileabethoxazole; D007501:Iron; C013905:cyclopentenone