Rational resolution of the isosteric enantiomers of 6,11-dihydrodibenzo[b,e]thiepin-11-ol and conversion to the two isosteric diastereoisomers of thecalcium channel blocker UK-74,756

Authors
Kemp, JEG Bass, RA Bordner, J Cross, PE Gammon, RF Price, JA
Citation
Jeg. Kemp et al., Rational resolution of the isosteric enantiomers of 6,11-dihydrodibenzo[b,e]thiepin-11-ol and conversion to the two isosteric diastereoisomers of thecalcium channel blocker UK-74,756, TETRAHEDR-A, 12(7), 2001, pp. 975-978
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
7
Year of publication
2001
Pages
975 - 978
Database
ISI
SICI code
0957-4166(20010508)12:7<975:RROTIE>2.0.ZU;2-C
Abstract
Sulfoxidation of the (+)-Noe-lactol derivative of racemic 6,11-dihydrodiben zo[h,e]thiepin-11-ol broke the isosterism and converted an inseparable mixt ure of two compounds into a separable mixture of four. X-Ray structural det ermination on one oi these and subsequent manipulation provided resolved 6, 11-dihydrodibenzo[b,e]thiepin-11-ol auld all four sulfoxides in known confi gurations, and enabled the resolution by synthesis of the two isosteric dia stereoisomers of the calcium channel blocker UK-74,756. (C) 2001 Elsevier S cience Ltd. All rights reserved.