合成路线1

Methylation of bicyclic oxazolidine (XXIX) by means of LDA and MeI, followed by selenenylation with PhSeBr/LDA in THF and ozonolysis in CH2Cl2, affords unsaturated derivative (XXX). Treatment of (XXX) with Tbdms-OTf and 2,6-lutidine in CH2Cl2 yields silyloxypyrrole (XXXI), which is converted into (XXXII) by an aldol reaction with (II) in the presence of SnCl4 in Et2O. Acetylation of (XXXII) by means of Ac2O, pyridine followed by dihydroxylation with OsO4 and N-methylmorpholine N-oxide allows formation of diol (XXXIII), whose tertiary hydroxyl group is removed by means of N,N'-thiocarbonyldiimidazole, followed by reduction with Bu3SnH and catalytic AIBN in toluene to provide derivative (XXXIV). Treatment of (XXXIV) with NaOH in MeOH followed by hydrogenolysis over Pd/C in HCl yields derivative (XXXV), which is converted into (XXXVI) by protection of primary alcohol by means of Et3SiCl and acetylation of secondary alcohol by treatment with Ac2O in pyridine. Regeneration of primary alcohol by treatment of (XXXVI) with HF in CH3CN furnishes (XXXVII), which is then oxidized by means of Jones reagent to yield (XXXVIII). Finally, saponification of diacetate acid (XXXVIII) with NaOH gives lactam (X).