Studies towards the enantioselective synthesis of 5,6,8-trisubstituted amphibian indolizidine alkaloids via enaminone intermediates

2005 ◽  
Vol 3 (5) ◽  
pp. 836 ◽  
Author(s):  
Joseph P. Michael ◽  
Charles B. de Koning ◽  
Christiaan W. van der Westhuyzen
Keyword(s):  
Enantioselective Synthesis ◽  
Indolizidine Alkaloids

Efficient stereoselective syntheses of piperidine, pyrrolidine, and indolizidine alkaloids

2001 ◽  
Vol 73 (3) ◽  
pp. 573-578 ◽  
Author(s):  
Dieter Enders ◽  
Christoph Thiebes
Keyword(s):  
Double Bond ◽  
Enantioselective Synthesis ◽  
Mexican Bean Beetle ◽  
Indolizidine Alkaloids ◽  
Recent Advances ◽  
Bean Beetle ◽  
Pyrrolidine Alkaloids ◽  
Stereoselective Syntheses ◽  
Enantioselective Syntheses

Recent advances in the diastereo- and enantioselective synthesis of piperidine, pyrrolidine, and indolizidine alkaloids, based on the highly stereoselective 1,2-addition to the CN double bond of chiral aldehyde-SAMP/RAMP hydrazones, are described. The enantioselective syntheses of the pyrrolidine alkaloids bgugaine and (2S,12¢R)-2-(12¢-aminotridecyl)-pyrrolidine, a defense alkaloid of the Mexican bean beetle are reported. Furthermore, the SAMP/RAMP-hydrazone method was applied to the syntheses of two 5,8-disubstituted indolizidine alkaloids that have been extracted from neotropical poison-dart frogs. The a-alkylation of aldehyde-SAMP/RAMP hydrazones has been used in the enantioselective synthesis of two epimers of stenusine, a 3-substituted piperidine alkaloid and spreading reagent of the beetle Stenus comma.

Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides

2021 ◽  
Author(s):  
Xin-Ming Xu ◽  
Ming Xie ◽  
Jiazhu Li ◽  
Mei-Xiang Wang
Keyword(s):  
Indole Alkaloid ◽  
Enantioselective Synthesis ◽  
High Yield ◽  
Tandem Reaction ◽  
Indole Derivatives

An exquisite Pybox/Cu(OTf)2-catalyzed asymmetric tandem reaction of tertiary enamides was developed, which enabled the expeditious synthesis of indolizino[8,7-b]indole derivatives in high yield, excellent enantioselectivity and diastereoselectivity.

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