       Document 0122
 DOCN  M9640122
 TI    A new nucleophilic ring opening of an activated cyclopropane and a
       formal synthesis of (+/-)-carbovir.
 DT    9604
 AU    Tanimori S; Tsubota M; He M; Nakayama M; Department of Applied
       Biochemistry, College of Agriculture, Osaka; Prefecture University,
       Japan.
 SO    Biosci Biotechnol Biochem. 1995 Nov;59(11):2091-3. Unique Identifier :
       AIDSLINE MED/96100939
 AB    The reaction of bicyclo[3.1.0]hexane 1, possessing a doubly activated
       cyclopropane ring, with acetic acid and potassium acetate in DMSO
       proceeded smoothly to give the adduct 2 in good yield. A formal total
       synthesis of the potent anti-HIV agent (+/-)-carbovir (9) was done by
       converting 2 into a known precursor 8 in 8 steps via allyl alcohol 7
       including the regioselective introduction of a double bond (4 to 5) and
       attachment of the nucleobase using the Mitsunobu reaction (7 to 8).
 DE    Antiviral Agents/*CHEMICAL SYNTHESIS/PHARMACOLOGY
       Cyclopropanes/*CHEMISTRY  Dideoxynucleosides/*CHEMICAL
       SYNTHESIS/PHARMACOLOGY  HIV/DRUG EFFECTS  Nuclear Magnetic Resonance
       Spectrum Analysis, Mass  Support, Non-U.S. Gov't  JOURNAL ARTICLE

       SOURCE: National Library of Medicine.  NOTICE: This material may be
       protected by Copyright Law (Title 17, U.S.Code).

