Premium
A Short and Efficient Enantiomeric Synthesis of Antitumor Fused Tetrahydrofurans
Author(s) -
Pinacho Crisóstomo Fernando R.,
Padrón José M.,
Martín Tomás,
Villar Jesús,
Martín Víctor S.
Publication year - 2006
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.200500842
Subject(s) - chemistry , sharpless asymmetric dihydroxylation , sharpless epoxidation , enantiomer , stereocenter , stereoselectivity , stereochemistry , tetrahydrofuran , bicyclic molecule , enantiomeric excess , dihydroxylation , epoxide , enantioselective synthesis , organic chemistry , solvent , catalysis
A short and efficient enantiomeric synthesis of fused tetrahydrofuran derivatives is reported. The methodology is based on a regio‐ and stereoselective double exo ‐cyclization of enantiomeric bis‐epoxy‐diols. The six stereocenters of the bis‐epoxy diols were introduced by the application of Katsuki–Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. In vitro cytotoxicities on HL60 human promyelocytic leukemia cells were determined for the bicyclic products. Active products showed exceptionally steep dose–response curves and DNA laddering. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)