60890-29-1Relevant articles and documents
Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines
Chen, Li-Jun,Li, Wei,Shen, Bao-Chun,Sun, Zhong-Wen,Xie, Hui-Ding,Zhang, Cong-Cong
, p. 8607 - 8612 (2021/10/20)
The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).
Synthesis of the Alkaloids, 3',4'-Dimethoxy-2-82-piperidyl)acetophenone, Julandine, and Cryptopleurine
Cragg, John E.,Herbert, Richard B.
, p. 2487 - 2490 (2007/10/02)
Condensation of (3,4-dimethoxybenzoyl)acetic acid (2) with enzyme-generated 3,4,5,6-tetrahydropyridine (3) gives 3',4'-dimethoxy-2-(2-piperidyl)acetophenone (4) which, by reaction with p-methoxyphenylacetaldehyde followed by titanium(IV) chloride- or silicon(IV) chloride-catalysed cyclisation of the resulting enamine (6), leads to julandine (7); thallium(III) trifluoroacetate oxidation of (7) gives cryptopleurine (8) and, as a very minor product, the isomer (9).
A New Synthesis of Septicine, a Secophenanthroindolizine Alkaloid
Mangla, V. K.,Bhakuni, D. S.
, p. 748 - 749 (2007/10/02)
Septicine , an alkaloid isolated from Ficus septica and Tylophora asthmatica, has been synthesized using 2-(3',4'-dimethoxyphenacyl)pyrrolidine (6) and 3,4-dimethoxy-phenylacetyl chloride (11) as the essential intermediates.Condensation of 6 and 11 affords 2-(3',4'-dimethoxyphenacyl)-N-(3'',4''-dimethoxyphenylacetyl)pyrrolidine (12) which on treatment with potassium-t-butoxide furnishes 6,7-di-(3',4'-dimethoxyphenyl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine (13).LAH reduction of 13 affords septicine (1), identical (co-TLC, IR, PMR, m.m.p.) with a natural sample.