Synthesis of C21-C41 fragment of the reported structure of Neaumycin B

초록

Stereoselective synthesis of the C-21-C-41 fragment 4 of the reported structure of Neaumycin B(1), a 28-membered macrolide compound with 19-chiral centers and 6,6-spiroketal structure, has been described. C-21-C-27 fragment 5 was synthesized from the commercially available (S)-Roche ester 7 using stereoselective allylation and Brown anti-crotylation as key steps. C-28-C-41 fragment 6 was constructed from chiral oxazolidinone auxiliary 13 using Evans syn-aldol reaction, diastereoselective epoxidation, and (S)-CBS reduction as key steps. Finally, boron-mediated acetate aldol reaction of 5 and 6 led to the synthesis of C-21-C(41 )fragment 4 for the reported structure of Neaumycin B (1). Stereoselective synthesis of the C21-C41 fragment 4. image

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