Lister Troy, Perkins Michael V
School of Chemistry, Physics and Earth Sciences, Flinders University, G. P. O. Box 2100, S.A. 5001, Australia.
Org Lett. 2006 Apr 27;8(9):1827-30. doi: 10.1021/ol060347s.
[reaction: see text] The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.
[反应:见正文] 多拉布醇的受保护前体30是通过DBU诱导的酯形成逆克莱森反应生成的。22中存在的所需直链碳链是通过立体选择性锂羟醛反应合成的。必要的醛和酮片段是使用与(S)-乳酸乙酯衍生的酮13进行立体控制的羟醛反应合成的。