Synthesis of the C1-C18 fragment of Neaumycin B

초록

Stereoselective synthesis of the C-1-C-18 fragment 2 of Neaumycin B (1), 28-membered macrolide compound with 19-chiral centers and 6,6-spiroketal structure, has been described. Brown syn-crotylation and olefin metathesis reaction were used as key steps from (R)-roche ester in the synthesis of C-8-C-18 fragment 3. C-1-C-7 fragment 4 was constructed from 1,3-propanediol using diastereoselective allylation, syn-aldol reaction, and olefin metathesis reaction as key steps. Finally, NHK reaction and (S)-CBS reduction as key steps led to the of synthesis of C-1-C-18 fragment 2 of Neaumycin B (1).

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