Total synthesis of (+/-)-crinine via the regioselective Stille coupling and Diels-Alder reaction of 3,5-dibromo-2-pyrone.
The regioselective synthesis and Diels-Alder cycloaddition of 3-(3,4-methylenedioxyphenyl)-5-bromo-2-pyrone provided a new synthetic route to crinine. The vinyl bromide group can be used as a handle for further derivatization.
Tam
Nguyen Thanh
NT
Department of Chemistry, Hanyang University, Seoul, Korea 133-791.
Cho
Cheon-Gyu
CG
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism
C450850:3,5-dibromo-2-pyrone; D047151:Amaryllidaceae Alkaloids; D011753:Pyrones; C528221:crinine