Asymmetric synthesis of (-)-aurantioclavine via palladium-catalyzed intramolecular allylic amination.
The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.
Graduate School of Pharmaceutical Sciences, Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Satoshi
S
Suetsugu
Hiromi
H
Nishiguchi
Chihiro
C
Tsukano
Yoshiji
Y
Takemoto
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D004876:Ergot Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D004876:Ergot Alkaloids; C551152:aurantioclavine; D010165:Palladium