Asymmetric syntheses of diarylheptanoid natural products (-)-centrolobine and (-)-de-O-methylcentrolobine via hetero-Diels-Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate]

作者：Washio Takuya; Yamaguchi Reika; Abe Takumi; Nambu Hisanori; Anada Masahiro; Hashimoto Shunichi^*

来源：Tetrahedron, 2007, 63(48): 12037-12046.

DOI：10.1016/j.tet.2007.09.003

• diarylheptanoids
• hetero-Diels-Alder reaction
• (-)-centrolobine
• (-)-de-O-methylcentrolobine
• chiral Rh(II) catalyst

Catalytic asymmetric syntheses of (-)-centrolobine and (-)-de-O-methylcentrolobine have been achieved, incorporating a hetero-Diels-Alder (HDA) reaction between 4-aryl-2-silyloxy-1,3-butadienes and phenylpropargyl aldehyde derivatives as a key step. The HDA reaction using dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), as a chiral Lewis acid catalyst provides exclusively cis-2,6-disubstituted tetrahydropyran-4-ones in up to 93% ee.

• 出版日期2007-11-26