三氧化二卡林 DC-45-A1、A、D、C 和 C7″-表-C 的全合成及三氧化二卡林 C 的结构全归属
Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-epi-C and Full Structural Assignment of Trioxacarcin C.
机构信息
Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
出版信息
J Am Chem Soc. 2016 Mar 9;138(9):3118-24. doi: 10.1021/jacs.5b12687. Epub 2016 Feb 24.
Trioxacarcins DC-45-A2, DC-45-A1, A, D, C7″-epi-C, and C have been synthesized through stereoselective strategies involving BF3·Et2O-catalyzed ketone-epoxide opening and gold-catalyzed glycosylation reactions, and the full structural assignment of trioxacacin C was deciphered via the syntheses of both of its C7″ epimers. The gathered knowledge sets the foundation for the design, synthesis, and biological evalution of analogues of these natural products as potential payloads for antibody-drug conjugates and other delivery systems for targeted and personalized cancer chemotherapy.
三氧化杀癌素 DC-45-A2、DC-45-A1、A、D、C7″-表-C 和 C 已通过立体选择性策略合成，其中包括 BF3·Et2O 催化的酮-环氧化物开环和金催化的糖苷化反应，并且通过合成这两种 C7″ 差向异构体，确定了三氧化杀癌素 C 的完整结构。这些天然产物的类似物的设计、合成和生物学评估为抗体药物偶联物和其他靶向和个性化癌症化疗的递药系统提供了潜在的有效载荷，这些知识为这些类似物的设计、合成和生物学评估奠定了基础。
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