483-04-5Relevant articles and documents
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Gutzwiller et al.
, p. 5907 (1971)
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Bader,Schwarz
, p. 1594,1597 (1952)
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A Radical Cascade Enabling Collective Syntheses of Natural Products
Wang, Xiaobei,Xia, Dongliang,Qin, Wenfang,Zhou, Ruijie,Zhou, Xiaohan,Zhou, Qilong,Liu, Wentao,Dai, Xiang,Wang, Huijing,Wang, Shuqing,Tan, Ling,Zhang, Dan,Song, Hao,Liu, Xiao-Yu,Qin, Yong
, p. 803 - 816 (2017/06/13)
Natural products have long been important inspirations for the development of chemical methodologies, theories, and technologies, and ultimately, discoveries of new drugs and materials. Chemical syntheses have traditionally yielded individual or small groups of natural products; however, methodology development allowing the synthesis of a large collection of natural products remains scarce. Here, we report an efficient photocatalytic radical cascade method that enables access to libraries of chiral and multiple-ring-fused tetrahydrocarbolinones. The radical cascade can controllably introduce complexity and functionality into products with excellent chemo-, regio-, and diastereoselectivity. The power of this distinct method has been demonstrated by the efficient syntheses of 33 monoterpenoid indole alkaloids belonging to four families.
Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis
Younai, Ashkaan,Zeng, Bi-Shun,Meltzer, Herbert Y.,Scheidt, Karl A.
, p. 6900 - 6904 (2015/06/08)
Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.
Biomimetic synthesis of monoterpenoid indole alkaloids from aglucones of secologanin derivatives: pH controlled product selectivity
Brown
, p. 609 - 616 (2007/10/03)
Variation of the pH for hydrolysis of secologanin derivatives with β-glucosidase controls rearrangement of the aglucone to afford different products, and hence stercoselective syntheses of heteroyohimbine, yohimbine and Aspidosperma-type alkaloids; with baker's yeast chemoselective reduction can also be achieved to give a precursor for antirhine and related alkaloids.
