Total Syntheses of (+)-Grandilodine C and (+)-Lapidilectine B and Determination of their Absolute Stereochemistry

2016 ◽  
Vol 55 (10) ◽  
pp. 3473-3476 ◽  
Author(s):  
Masaya Nakajima ◽  
Shigeru Arai ◽  
Atsushi Nishida
Keyword(s):  
Total Syntheses ◽  
Absolute Stereochemistry ◽  
Lapidilectine B

Total Syntheses of (+)-Echinopine A and B: Determination of Absolute Stereochemistry

2009 ◽  
Vol 11 (22) ◽  
pp. 5306-5309 ◽  
Author(s):  
Thomas Magauer ◽  
Johann Mulzer ◽  
Konrad Tiefenbacher
Keyword(s):  
Total Syntheses ◽  
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.

Determination of the Absolute Stereochemistry of Cyclosmenospongine

2003 ◽  
Vol 66 (9) ◽  
pp. 1263-1265 ◽  
Author(s):  
Natalia K. Utkina ◽  
Vladimir A. Denisenko ◽  
Olga V. Scholokova ◽  
Aleksandra E. Makarchenko
Keyword(s):  
The Absolute ◽  
Absolute Stereochemistry

First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

2006 ◽  
Vol 47 (37) ◽  
pp. 6537-6540 ◽  
Author(s):  
G.V.M. Sharma ◽  
K. Laxmi Reddy ◽  
J. Janardhan Reddy
Keyword(s):  
The Absolute ◽  
Absolute Stereochemistry

Enantioselective Synthesis of Poison-Frog Alkaloid 237D and Determination of Absolute Stereochemistry

Heterocycles ◽  
2005 ◽  
Vol 65 (1) ◽  
pp. 5 ◽  
Author(s):  
Naoki Toyooka ◽  
Hideo Nemoto ◽  
Masashi Kawasaki ◽  
John W. Daly ◽  
Thomas F. Spande ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Poison Frog ◽  
Absolute Stereochemistry
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