Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.
Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.
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DOI：
10.1002/anie.202103553
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发表时间：
2021-06-01
期刊：
影响因子：
--
通讯作者：
Dong G
中科院分区：
文献类型：
--
作者：
Hou SH;Prichina AY;Dong G
Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (−)-thebainone A, capitalized on an enantioselective C−C bond activation and a C−O bond cleavage reaction. The Rh-catalyzed asymmetric ‘cut-and-sew’ transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allows efficient construction of the fused A/B/C rings and the all-carbon quaternary center of the natural product. The newly optimized conditions show a broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of the boron-mediated ether bond cleavage, synthesis of the morphine-alkaloid (−)-thebainone A has been completed with two complementary routes. Asymmetric total synthesis of morphine alkaloid (−)-thebainone A has been accomplished for the first time in 13 (and 14) steps from commercially available starting materials. The synthesis features a deconstructive strategy through cleaving relatively inert C‒C and C‒O bonds to build more complex scaffolds.
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