A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir
Graphical abstract
Section snippets
Acknowledgements
The work has been supported by a grant (to S.B.M.) from the Department of Science and Technology (Govt. of India). The authors gratefully acknowledge the Council of Scientific and Industrial Research (CSIR) for providing Research Fellowships (to B.G.R. and P.K.J.) and Emeritus Scientist Scheme (to B.A.).
References and notes (14)
- et al.
Tetrahedron
(1992)et al.Tetrahedron
(1994)Tetrahedron
(1998)et al.Chem. Rev.
(1992)et al.Chem. Rev.
(2000) - et al.
Tetrahedron Lett.
(1995)et al.J. Org. Chem.
(1994)et al.J. Chem. Soc., Perkin Trans. 1
(1992)et al.J. Am. Chem. Soc.
(1992)et al.J. Chem. Soc., Perkin Trans. 1
(1994)et al.J. Org. Chem.
(1996)et al.Helv. Chim. Acta
(1994)et al.Tetrahedron: Asymmetry
(1994) - et al.
Antimicrob. Agents Chemother.
(1997) - et al.
J. Org. Chem.
(2005)et al.Tetrahedron Lett.
(2004)et al.J. Org. Chem.
(2001)et al.J. Org. Chem.
(2006) - et al.
J. Org. Chem.
(1996)et al.J. Med. Chem.
(1992) - et al.
Chem. Soc. Rev.
(1995)
Cited by (11)
Advances in the synthesis of antiviral agents from carbohydrate-derived chiral pools
2023, Journal of Carbohydrate ChemistryRegioselective synthesis of 3-deazacarbovir and its 3-deaza-adenosine analogues
2009, TetrahedronCitation Excerpt :In our efforts to further explore the carbocyclic 3-deazanucleoside, it was of interest to synthesize hitherto unknown 3-deazacarbovir 1 and carbocyclic 2′,3′-didehydro-2′,3′-dideoxy-3-deaza-adenosine analogs 2 and 3. Several synthetic methodologies have been reported for the synthesis of carbovir19–28 among them palladium catalyzed coupling and convergent approach to construct base ring are most prominent. Our group has reported the synthesis of l-carbovir using Mitsunobu coupling.29
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the Year 2007
2009, Coordination Chemistry ReviewsEfficient Greener Visible-Light-Catalyzed Debenzylation of Benzyl Ethers and Esters: A Gateway to Wider Exploitation of Stable Benzyl Protecting Groups
2022, Asian Journal of Organic ChemistryApplication of Pauson-Khand reaction in the total synthesis of terpenes
2021, RSC AdvancesOlefin ring-closing metathesis
2016, Organic Reactions