Total Syntheses of Ainsliadimer B and Gochnatiolides A and B

Authors

  • Dongliang Xia,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
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    • These authors contributed equally to this work

  • Yu Du,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
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    • These authors contributed equally to this work

  • Zhi Yi,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
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  • Hao Song,

    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
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  • Prof. Dr. Yong Qin

    Corresponding author
    1. Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
    2. Innovative Drug Research Centre and College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 401331 (P.R. China), Fax: (+86) 23-65678750
    • Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041 (P.R. China), Fax: (+86) 28-85503842
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Abstract

original image

Oh my goch: The total syntheses of ainsliadimer B and gochnatiolides A and B from α-santonin have been accomplished in 25 steps with approximately 1 % overall yield. A Diels–Alder reaction of natural dehydrozaluzanin C with a monomeric guaianolide derivative allows stereoselective assembly of a dimeric gochnatiolide-type skeleton with the required stereochemistry and preinstalled functionalities for the synthesis of dimeric ainsliadimer B and gochnatiolides A and B (see scheme).

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