Del Valle Juan R, Goodman Murray
Department of Chemistry and Biochemistry, University of California-San Diego, La Jolla, CA 93027, USA.
J Org Chem. 2004 Dec 10;69(25):8946-8. doi: 10.1021/jo0485738.
A condensation--ring-close--ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.
采用缩合-闭环-开环序列，从易于获得的手性合成子出发，合成了正交保护的内消旋-2,6-二氨基庚二酸。适当保护的L-烯丙基甘氨酸和D-乙烯基甘醇衍生物缩合后，进行格拉布闭环复分解反应，生成关键的内酰胺中间体。该策略已应用于高效免疫刺激肽FK565的简洁全合成。
