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Synthesis of 3′‐Deoxyribolactones using a Hydrolysis‐Induced Lactonization Cascade Reaction of Epoxy Cyanohydrins
Author(s) -
Vugts Danielle J.,
Aktas Halil,
AlMafraji Kanar,
de Kanter Frans J. J.,
Ruijter Eelco,
Groen Marinus B.,
Orru Romano V. A.
Publication year - 2008
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/ejoc.200701152
Subject(s) - chemistry , hydrolysis , cascade , yield (engineering) , cascade reaction , organic chemistry , epoxy , combinatorial chemistry , catalysis , chromatography , materials science , metallurgy
The synthesis of 3′‐deoxyribolactones was accomplished in a few steps from the commercially available 3‐decyn‐1‐ol in 44 % overall yield. The key transformation comprises a one‐pot four‐reaction hydrolysis‐induced lactonization cascade. The strategy was employed to efficiently access optically active 5′‐chloro‐3′‐deoxyribolactones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)