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Versatile Construction of 6-Substituted cis-2,8-Dioxabicyclo[3.3.0]octan-3-ones: Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2017-05-17 00:00:00 , DOI: 10.1021/jacs.7b04265 Yuriy Slutskyy 1 , Christopher R. Jamison 1 , Peng Zhao 1 , Juyeol Lee 1 , Young Ho Rhee 2 , Larry E. Overman 1
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2017-05-17 00:00:00 , DOI: 10.1021/jacs.7b04265 Yuriy Slutskyy 1 , Christopher R. Jamison 1 , Peng Zhao 1 , Juyeol Lee 1 , Young Ho Rhee 2 , Larry E. Overman 1
Affiliation
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.
中文翻译:
6取代的顺式-2,8-二恶双环[3.3.0] octan-3-one的多功能构建:Cheloviolenes A和B和Dendrillolide C的短对映选择性全合成
描述了6-取代的顺式-2,8-二氧杂双环[3.3.0] octan-3-ones的短对映选择性合成。关键步骤是将由叔醇直接生成的叔自由基与3-氯-5-烷氧基丁烯内酯偶联。该策略适用于三种重排的海绵状二萜类化合物的可扩展的14-15步合成:螯合物A和B和树突状内酯C。
更新日期:2017-05-23
中文翻译:
6取代的顺式-2,8-二恶双环[3.3.0] octan-3-one的多功能构建:Cheloviolenes A和B和Dendrillolide C的短对映选择性全合成
描述了6-取代的顺式-2,8-二氧杂双环[3.3.0] octan-3-ones的短对映选择性合成。关键步骤是将由叔醇直接生成的叔自由基与3-氯-5-烷氧基丁烯内酯偶联。该策略适用于三种重排的海绵状二萜类化合物的可扩展的14-15步合成:螯合物A和B和树突状内酯C。