Crimmins Michael T, DeBaillie Amy C
Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
Org Lett. 2003 Aug 21;5(17):3009-11. doi: 10.1021/ol034923l.
[reactiojn: see text] The enantioselective synthesis of (+)-rogioloxepane A has been achieved in 21 steps from 1,5-hexadien-3-ol. The key steps in the synthesis are an asymmetric glycolate alkylation leading to the diene 2 and a subsequent ring-closing metathesis to construct the oxepene core.
[反应:见正文] 已从1,5-己二烯-3-醇经21步实现了(+)-罗吉洛环氧烷A的对映选择性合成。合成中的关键步骤是导致二烯2的不对称乙醇酸烷基化以及随后用于构建氧杂环庚三烯核心的闭环复分解反应。