Asymmetric Total Synthesis of Oxazolomycins B and C. Issue 41 (4th June 2021)

• Record Type: Journal Article
• Authors: Song, Yeonghun; Kim, Jae Hyun; Kim, Young Chan; Kim, Sanghee
• Is Part Of: Chemistry. Volume 27:Issue 41(2021)
• Page Start: 10731
• Page End: 10736
• Publication Date: 2021-06-04
• Subjects: antibiotics -- natural products -- structure elucidation -- synthesis design -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202101341
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Efforts towards the first total synthesis of (−)‐oxazolomycin B and (+)‐oxazolomycin C from the intermediate of our previous synthesis of (+)‐neoxazolomycin are reported. The syntheses were achieved in a longest linear sequence of 25 steps from the amino acid serine in 3.6 and 2.7 % overall yields, respectively. The efficiency of our approach is derived from silyl triflate‐mediated reductive oxazolidine ring‐opening and Fürstner's Ru‐catalyzed hydrosilylation and protodesilylation reactions. The obtained spectra and optical rotations were in good agreement with those of natural products, thus confirming the structures. Abstract : Synthesis confirms structures : The first total synthesis of (−)‐oxazolomycin B and (+)‐oxazolomycin C was achieved in a longest linear sequence of 25 steps from the amino acid serine in 3.6 and 2.7 % overall yield, respectively. The completion of the total synthesis showed that the hypothesized structures of the natural products are correct.