Determination of the Absolute Stereochemistry and Asymmetric Total Synthesis of Madindolines A (I) and B (II): A Practical Improvement to a Second-Generation Approach from the First-Generation.

ChemInform ◽  
2005 ◽  
Vol 36 (42) ◽  
Author(s):  
Tomoyasu Hirose ◽  
Toshiaki Sunazuka ◽  
Daisuke Yamamoto ◽  
Naoto Kojima ◽  
Tatsuya Shirahata ◽  
...  
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Second Generation ◽  
Asymmetric Total Synthesis ◽  
The Absolute ◽  
Absolute Stereochemistry

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute

Total synthesis and determination of the absolute stereochemistry of the squalene synthase inhibitors CJ-13,981 and CJ-13,982

2009 ◽  
Vol 50 (26) ◽  
pp. 3388-3390 ◽  
Author(s):  
Frederick Calo ◽  
Alexander Bondke ◽  
Jeffery Richardson ◽  
Andrew J.P. White ◽  
Anthony G.M. Barrett
Keyword(s):  
Total Synthesis ◽  
Squalene Synthase ◽  
The Absolute ◽  
Absolute Stereochemistry

scholarly journals Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Tetsuya Sengoku ◽  
Jolanta Wierzejska ◽  
Masaki Takahashi ◽  
Hidemi Yoda
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Ring System ◽  
Piperidine Ring ◽  
Total Syntheses ◽  
Asymmetric Dihydroxylation ◽  
Biological Studies ◽  
The Common ◽  
Absolute Stereochemistry

Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples which would pave the way for further biological studies.

First Asymmetric Total Synthesis of Synerazol, an Antifungal Antibiotic, and Determination of Its Absolute Stereochemistry

2005 ◽  
Vol 70 (14) ◽  
pp. 5643-5654 ◽  
Author(s):  
Yujiro Hayashi ◽  
Mitsuru Shoji ◽  
Takasuke Mukaiyama ◽  
Hiroaki Gotoh ◽  
Shinpei Yamaguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Antifungal Antibiotic ◽  
Absolute Stereochemistry
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