Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University Medical Center, Nashville, Tennessee 37232, USA.
Org Lett. 2010 Mar 5;12(5):1048-51. doi: 10.1021/ol100034p.
The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1-C25 Diels-Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels-Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.
描述了通过评估提议的生物合成来实现海洋霉素 A 和 B（一种来自链霉菌放线菌的新型螺氨基醇）的首次全合成。采用 8 步反应，以 5.1%的总收率制备了假设的生物合成 C1-C25 Diels-Alder 底物；然而，提议的仿生反电子需求杂 Diels-Alder 反应未能提供海洋霉素核心。分子力学支持这一观察结果。
