213403-17-9Relevant academic research and scientific papers
The first total synthesis of concanamycin F (concanolide A)
Toshima,Jyojima,Miyamoto,Katohno,Nakata,Matsumura
, p. 1708 - 1715 (2001)
A highly stereoselective total synthesis of the macrolide antibiotic concanamycin F (1), a specific and potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 18-membered tetraenic lactone and β-hydroxyl hemiacetal side chain subunits. The C1-C19 18-membered lactone aldehyde 4 was synthesized through the intermolecular Stille coupling of the C5-C13 vinyl iodide 24 and the C14-C19 vinyl stannane 25, followed by construction of the C1-C4 diene and macrolactonization. Synthesis of 4 via a second convergent route including the esterification of the C1-C13 vinyl iodide 45 and the C14-C19 vinyl stannane 47 followed by the intramolecular Stille coupling was also realized. The highly stereoselective aldol coupling of 4 and the C20-C28 ethyl ketone 5 followed by desilylation provided 1 which was identical with natural concanamycin F.
Synthetic studies on concanamycin A: Synthesis of the C5~C13 and C20~C28 segments
Jyojima, Takaaki,Katohno, Masataka,Miyamoto, Naoki,Nakata, Masaya,Matsumura, Shuichi,Toshima, Kazunobu
, p. 6003 - 6006 (2007/10/03)
The enantioselective synthesis of the C5~C13 (2) and C20~C28 (3) segments, which are promising synthetic intermediates toward the total synthesis of the 18-membered macrolide antibiotic, concanamycin A (1), were described.
