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Deoxyhydantocidin: Synthesis by Base‐Catalyzed Spiro Cyclization and Interconversion with the 1′‐Epimer
Author(s) -
Renard Annabelle,
Kotera Mitsuharu,
Brochier MarieChristine,
Lhomme Jean
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:9<1831::aid-ejoc1831>3.0.co;2-s
Subject(s) - chemistry , epimer , phosphonate , base (topology) , catalysis , nuclear magnetic resonance spectroscopy , derivative (finance) , stereochemistry , condensation , condensation reaction , organic chemistry , mathematical analysis , mathematics , physics , financial economics , economics , thermodynamics
Syntheses of the spiro nucleosides 2′‐deoxyhydantocidin 3a and its 1′‐epimer 3b are described. The newly developed route involves a Horner‐Wadsworth‐Emmons condensation of the phosphonate 16 with the erythrose derivative 15 affording a mixture of six isomers which was fully assigned by NMR spectroscopy. The mixture was directly converted into the final compounds in an efficient base‐catalyzed cyclization reaction. A base‐catalyzed interconversion between the two isomers was observed.