Li Fangzheng, Warshakoon Namal C, Miller Marvin J
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
J Org Chem. 2004 Dec 10;69(25):8836-41. doi: 10.1021/jo048606j.
Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.
通过分子内羟醛缩合策略，从容易获得的氨基环戊烯醇（-）-7出发，实现了（+）-链唑啉1及其更稳定的二氢衍生物2的简洁全合成。合成步骤包括还原胺化、立体选择性环氧化、分子内羟醛（和缩合）反应以及维蒂希反应。从氨基环戊烯醇（-）-7合成二氢衍生物2的总收率约为7%，共14步反应。
