对映选择合成
立体中心
化学
催化作用
邻接
内酯
立体化学
铜
组合化学
有机化学
作者
Jin Cui,Raphaël Oriez,Hidetoshi Noda,Takumi Watanabe,Masakatsu Shibasaki
标识
DOI:10.1002/anie.202203128
摘要
Vicinal oxygen-containing tetra- and tri-substituted stereocenters exist widely in chromanone lactone and tetrahydroxanthone natural products. Their enantioselective construction in a single step remains elusive and poses a formidable challenge for chemical synthesis. Here, we report the first copper(I)-catalyzed asymmetric vinylogous additions of siloxyfurans to 2-ester-substituted chromones, which enable concise and enantioselective assembly of chromanone lactones. Both syn and anti adducts can be accessed with excellent diastereo- and enantioselectivity by judicious choice of the chiral ligands. Our approach allowed for the efficient synthesis of (-)-blennolide B with precise stereochemical control, which provides a formal synthesis of secalonic acid A.
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