Efficient synthesis of carbocyclic nucleoside, (+/-)-homocarbovir via pi-allylpalladium complex formation from the allyl-N,N-ditosylimide substrate.
The synthesis of a carbovir analogue, (+/-)-homocarbovir (3) was achieved from norbornadiene (4) in seven steps and 27% overall yield. This route involves a Meinwald-type rearrangement, an acid-hydrolysis of N-tosyl bicyclic enamine 5, and a Pd(0)-catalyzed coupling reaction.
Rhee
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Department of Chemistry, Hanyang University, Ansan, Korea. HRhee@mail.hanyang.ac.kr
Yoon
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D
Jung
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ME
D000498:Allyl Compounds / Q000737:chemistry*; D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002522:Chlorocebus aethiops; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000737:chemistry; D006678:HIV / Q000187:drug effects; D015368:Human T-lymphotropic virus 1 / Q000187:drug effects; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D018139:Simplexvirus / Q000187:drug effects; D013601:T-Lymphocytes / Q000821:virology; D014105:Tosyl Compounds / Q000737:chemistry*; D014709:Vero Cells
D000498:Allyl Compounds; D019380:Anti-HIV Agents; D000998:Antiviral Agents; D015224:Dideoxynucleosides; D009942:Organometallic Compounds; D014105:Tosyl Compounds; C412236:homocarbovir; C057503:carbovir; D010165:Palladium; D003849:Deoxyguanosine