Studies on a total synthesis of plakotenin: Synthesis of optically active trans-hydrindanes by diastereoselective asymmetric intramolecular Diels-Alder reaction

Authors
Ishizaki, M Hara, Y Kojima, S Hoshino, O
Citation
M. Ishizaki et al., Studies on a total synthesis of plakotenin: Synthesis of optically active trans-hydrindanes by diastereoselective asymmetric intramolecular Diels-Alder reaction, HETEROCYCLE, 50(2), 1999, pp. 779-790
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
2
Year of publication
1999
Pages
779 - 790
Database
ISI
SICI code
0385-5414(19990401)50:2<779:SOATSO>2.0.ZU;2-L
Abstract
Diastereoselective asymmetric intramolecular Diels-Alder reaction of 5,5-(t rimethylenedithio)-2(E),7(E),9-decatrienoyl amides (13a-e) having various c hiral auxiliaries was performed to give optically active trans-hydrindanes, which would be an important intermediate for a total synthesis of plakoten in (1), was described. In the several chiral auxiliaries, Saigo's oxazolidi none was found to give trans-hydrindane (15a) in the highest stereoselectiv ity (96% e.e.), after conversion to benzyl ester.