The Total Synthesis of Spermine Alkaloid Kukoamine Bimesylate

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2669-2672
Author(s):  
Kai Dong
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Cyano Group ◽  
Michael Addition Reaction ◽  
Amino Groups ◽  
Competitive Reaction ◽  
12 Steps ◽  
Cyano Groups

The first total synthesis of kukoamine B bimesylate was completed from 1,4-diaminobutane dihydrochloride in 12 steps with a 11.4% overall yield, and all the steps could be carried out at a kilogram scale. The cyano groups were used as the precursor of amino groups to avoid the competitive reaction delicately. The aza-Michael addition reaction, amidation and hydrogenation of the cyano group sequence was streamlined as a general approach towards the synthesis of polyamine structures.

Asymmetric total synthesis of (+)-asenapine

2019 ◽  
Vol 17 (12) ◽  
pp. 3225-3231 ◽  
Author(s):  
Piotr Szcześniak ◽  
Olga Staszewska-Krajewska ◽  
Jacek Mlynarski
Keyword(s):  
Total Synthesis ◽  
Michael Addition ◽  
Addition Reaction ◽  
Reductive Cyclization ◽  
Michael Addition Reaction ◽  
Asymmetric Total Synthesis ◽  
Key Steps

Asymmetric total synthesis of (+)-asenapine involving the organocatalytic Michael addition reaction and subsequent Zn-promoted reductive cyclization as the key steps.

scholarly journals Michael Addition Reaction Catalyzed by Imidazolium Chloride to Protect Amino Groups and Construct Medium Ring Heterocycles

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4224
Author(s):  
Dai ◽  
Tian ◽  
Li ◽  
Shang ◽  
Luo ◽  
...  
Keyword(s):  
High Temperatures ◽  
Michael Addition ◽  
Low Temperatures ◽  
Addition Reaction ◽  
Membered Ring ◽  
Michael Addition Reaction ◽  
Amino Groups ◽  
Imidazolium Chloride ◽  
Medium Ring ◽  
The Michael Addition

An effective approach for amino protection and construction of a seven-membered ring has been developed. The method uses imidazolium chloride to carry out the Michael addition reaction at low temperatures and perform amino deprotection or construction of a seven-membered ring at high temperatures.

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

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