Synthesis of 2-Azabicyclo[m.n.0]-Alkanes and Their Application towards the Synthesis of Strychnos and Stemona Classes of Alkaloids

被引：2

作者：

Majumder, Binoy ^{[1
,2
]}

Pandey, Ganesh ^{[1
]}

机构：

[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India

[2] CSIR, Div Organ Chem, Natl Chem Lab, Pune 411008, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 25期

关键词：

Amines; Michael addition; Grignard reaction; Alkaloids; Natural products; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; INDOLE ALKALOIDS; STEREOSELECTIVE-SYNTHESIS; (-)-TUBIFOLINE; EFFICIENT; PATHWAY; ENTRY; (-)-DEHYDROTUBIFOLINE; HEXAHYDROINDOLES;

D O I：

10.1002/ejoc.202000507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Azabicyclo[m.n.0]alkane ring systems, the conceptual precursors towards the synthesis of Strychnos and Stemona classes of alkaloids, were synthesized from tert-butyl 2-(phenylsulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylate by alkyl Grignard reaction and intramolecular cyclisation of the in situ generated ring opening product 2. The synthesized cis-hexahydroindole 3 and cis-octahydro-benzo[b]azepine 5 scaffolds were utilized to construct the advanced intermediates 25 and 35, respectively, towards the synthesis of the corresponding Strychnos and Stemona classes of alkaloids.

引用

页码：3883 / 3888

页数：6

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