TOTAL SYNTHESIS OF C-31-METHYL KETONE APOCAROTENOIDS .4. FIRST TOTAL SYNTHESIS OF (3S,5R,6R)-PARACENTRONE

Authors
HAUGAN JA
Citation
Ja. Haugan, TOTAL SYNTHESIS OF C-31-METHYL KETONE APOCAROTENOIDS .4. FIRST TOTAL SYNTHESIS OF (3S,5R,6R)-PARACENTRONE, Journal of the Chemical Society. Perkin transactions. I, (18), 1997, pp. 2731-2737
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
18
Year of publication
1997
Pages
2731 - 2737
Database
ISI
SICI code
0300-922X(1997):18<2731:TSOCKA>2.0.ZU;2-R
Abstract
Optically active (all-E)-(3S,5R,6R)-paracentrone has been prepared by total synthesis for the first time, in 3% overall yield over 13 linear steps from the readily available (4R,6R)-actinol, (2E)-3-methylpent-2 -en-4-yn-1-ol, (all-E)-2,7-dimethylocta-2,4,6-triene-1,8-dial and 1,1- dimethoxypropan-2-one. All spectral data for synthetic (all-E)-(3S,5R, 6R)-paracentrone are in accordance with data reported for the natural compound.