Evolution of the Total Synthesis of (−)-Okilactomycin Exploiting a Tandem Oxy-Cope Rearrangement/Oxidation, a Petasis−Ferrier Union/Rearrangement, and Ring-Closing Metathesis

• Published in: Journal of the American Chemical Society Vol. 131; no. 6; pp. 2348 - 2358
• Main Authors: Smith, Amos B, Bosanac, Todd, Basu, Kallol
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.02.2009; Amer Chemical Soc
• Subjects: Acetals - chemistry; Aldehydes - chemical synthesis; Aldehydes - chemistry; Chemistry; Chemistry, Multidisciplinary; Cyclization; Lactones - chemical synthesis; Macrocyclic Compounds - chemical synthesis; Oxidation-Reduction; Physical Sciences; Pyrans - chemical synthesis; Pyrans - chemistry; Science & Technology; Stereoisomerism; Streptomyces - chemistry; OXIDATION; DIELS-ALDER; NATURAL-PRODUCTS; CARBONYL-COMPOUNDS; ORGANIC HALIDES; ALDEHYDES; CLAISEN REARRANGEMENT; SELENIUM DIOXIDE; DERIVATIVES; OKILACTOMYCIN

An effective, asymmetric total synthesis of the antitumor antibiotic (−)-okilactomycin (1), as well as assignment of the absolute configuration, has been achieved exploiting a convergent strategy. Highlights of the synthesis include a diastereoselective oxy-Cope rearrangement/oxidation sequence to i...