OPTICALLY-ACTIVE CYCLOBUTANONE CHEMISTRY - SYNTHESIS OF (-)-CYCLOBUT-A AND (+ -)-3'-EPI-CYCLOBUT-A/

Authors
BROWN B HEGEDUS LS
Citation
B. Brown et Ls. Hegedus, OPTICALLY-ACTIVE CYCLOBUTANONE CHEMISTRY - SYNTHESIS OF (-)-CYCLOBUT-A AND (+ -)-3'-EPI-CYCLOBUT-A/, Journal of organic chemistry, 63(22), 1998, pp. 8012-8018
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
22
Year of publication
1998
Pages
8012 - 8018
Database
ISI
SICI code
0022-3263(1998)63:22<8012:OCC-SO>2.0.ZU;2-V
Abstract
The carbocyclic nucleoside analogues (-)-cyclobut-A and (+/-)-3'-epi-c yclobut-A were synthesized utilizing photolysis of the (benzyloxymethy l)(methoxy) chromium carbene complex 4 with optically active ene-carba mate 5 to produce the corresponding optically active alpha,alpha-disub stituted cyclobutanone 6. Stereoselective removal of the alpha-ethoxy group with inversion gave cyclobutanone 7, which was converted by exis ting methodology to the title compounds.