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A new nucleophilic ring opening of an activated cyclopropane and a formal synthesis of (+/-)-carbovir
- Source :
- Bioscience, biotechnology, and biochemistry. 59(11)
- Publication Year :
- 1995
-
Abstract
- 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).
- Subjects :
- chemistry.chemical_classification
Cyclopropanes
Magnetic Resonance Spectroscopy
Double bond
Stereochemistry
Organic Chemistry
Regioselectivity
Total synthesis
HIV
General Medicine
Applied Microbiology and Biotechnology
Biochemistry
Chemical synthesis
Antiviral Agents
Dideoxynucleosides
Mass Spectrometry
Analytical Chemistry
Cyclopropane
chemistry.chemical_compound
chemistry
Nucleophile
Mitsunobu reaction
Allyl alcohol
Molecular Biology
Biotechnology
Subjects
Details
- ISSN :
- 09168451
- Volume :
- 59
- Issue :
- 11
- Database :
- OpenAIRE
- Journal :
- Bioscience, biotechnology, and biochemistry
- Accession number :
- edsair.doi.dedup.....2576fb58091c16fd52f8f1f1e61effb9