Department of Chemistry, University of California, Irvine , Irvine, California 92697-2025, United States.
Department of Chemistry, Pohang University of Science and Technology , Hyoja-dong San 31, Pohang, Kyungbook 790-784, Republic of Korea.
J Am Chem Soc. 2017 May 31;139(21):7192-7195. doi: 10.1021/jacs.7b04265. Epub 2017 May 22.
A short enantioselective synthesis of 6-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-ones is described. The pivotal step is coupling of a tertiary radical generated directly from a tertiary alcohol with a 3-chloro-5-alkoxybutenolide. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids: cheloviolenes A and B and dendrillolide C.
本文描述了一种 6-取代的顺式-2,8-二氧杂双环[3.3.0]辛烷-3-酮的短对映选择性合成方法。关键步骤是直接从叔醇生成的叔自由基与 3-氯-5-烷氧基丁烯内酯的偶联。该策略应用于三个重排海绵二萜类化合物（cheloviolenes A 和 B 以及 dendrillolide C）的 14-15 步规模化合成。
