TOTAL SYNTHESIS OF C31-METHYL KETONE APOCAROTENOIDS - SINTAXANTHIN AND (3R)-3-HYDROXYSINTAXANTHIN

Authors
HAUGAN JA
Citation
Ja. Haugan, TOTAL SYNTHESIS OF C31-METHYL KETONE APOCAROTENOIDS - SINTAXANTHIN AND (3R)-3-HYDROXYSINTAXANTHIN, Acta chemica Scandinavica, 48(8), 1994, pp. 657-664
Citations number
29
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
48
Issue
8
Year of publication
1994
Pages
657 - 664
Database
ISI
SICI code
0904-213X(1994)48:8<657:TSOCKA>2.0.ZU;2-J
Abstract
The previously undescribed 2,7,11-trimethyl-12-oxo-2,4,6,8,10-tridecap entenal has been synthesised in 26% overall yield in six steps from th e readily available 3-methyl-2-penten-4-yn-1-ol and 2,7-dimethyl-2,4.6 -octatrienedial.This C-16-keto aldehyde was used in the first total sy nthesis of fully characterised (all-E)-sintaxanthin and optically acti ve (all-E)-(3R)-3-hydroxysintaxanthin. The C-16-keto aldehyde is a ver satile building block for any C31-methyl ketone apocarotenoid.