scholarly journals Corrigendum: Assignment of Relative Configuration of Desoxypropionates by1H NMR Spectroscopy: Method Development, Proof of Principle by Asymmetric Total Synthesis of Xylarinic Acid A and Applications

2012 ◽  
Vol 18 (45) ◽  
pp. 14226-14226
Author(s):  
Yvonne Schmidt ◽  
Konrad Lehr ◽  
Lucie Colas ◽  
Bernhard Breit
Keyword(s):  
Nmr Spectroscopy ◽  
Total Synthesis ◽  
Method Development ◽  
Spectroscopy Method ◽  
Asymmetric Total Synthesis ◽  
Relative Configuration ◽  
Proof Of Principle

scholarly journals Asymmetric Total Synthesis of (-)-Panacene and Correction of Its Relative Configuration.

ChemInform ◽  
2006 ◽  
Vol 37 (50) ◽  
Author(s):  
John Boukouvalas ◽  
Martin Pouliot ◽  
Joel Robichaud ◽  
Stephen MacNeil ◽  
Victor Snieckus
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Relative Configuration

Asymmetric Total Synthesis of (−)-Panacene and Correction of Its Relative Configuration

2006 ◽  
Vol 8 (16) ◽  
pp. 3597-3599 ◽  
Author(s):  
John Boukouvalas ◽  
Martin Pouliot ◽  
Joël Robichaud ◽  
Stephen MacNeil ◽  
Victor Snieckus
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Relative Configuration

Diastereoselective Reduction of Selected α-substituted β-keto Esters and the Assignment of the Relative Configuration by 1H-NMR Spectroscopy

2020 ◽  
Vol 07 ◽  
Author(s):  
Christian Trapp ◽  
Corinna Schuster ◽  
Chris Drewniok ◽  
Dieter Greif ◽  
Martin Hofrichter
Keyword(s):  
Nmr Spectroscopy ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Selective Reduction ◽  
Reducing Agents ◽  
Relative Configuration ◽  
Curtius Rearrangement ◽  
Keto Esters ◽  
Hydroxy Esters ◽  
Diastereoselective Reduction

Background:: Chiral β-hydroxy esters and α-substituted β-hydroxy esters represent versatile building blocks for pheromones, β-lactam antibiotics and 1,2- or 1,3-aminoalcohols. Objective:: Synthesis of versatile α-substituted β-keto esters and their diastereoselective reduction to the corresponding syn- or anti-α-substituted β-hydroxy esters. Assignment of the relative configuration by NMR-spectroscopy after a CURTIUS rearrangement of α-substituted β-keto esters to 4-substituted 5-methyloxazolidin-2-ones. Method:: Diastereoselective reduction was achieved by using different LEWIS acids (zinc, titanium and cerium) in combination with complex borohydrides as reducing agents. Assignment of the relative configuration was verified by 1H-NMR spectroscopy after CURTIUS-rearrangement of α-substituted β-hydroxy esters to 4-substituted 5-methyloxazolidin-2-ones. Results:: For the syn-selective reduction, titanium tetrachloride (TiCl4) in combination with a pyridine-borane complex (py BH3) led to diastereoselectivities up to 99% dr. High anti-selective reduction was achieved by using cerium trichloride (CeCl3) and steric hindered reducing agents such as lithium triethylborohydride (LiEt3BH). After CURTIUS-rearrangement of each α-substituted β-hydroxy ester to the corresponding 4-substituted 5-methyloxazolidin-2-one, the relative configuration was confirmed by 1H NMR-spectroscopy. Conclusion:: We have expanded the procedure of LEWIS acid-mediated diastereoselective reduction to bulky α-substituents such as the isopropyl group and the electron withdrawing phenyl ring.

ChemInform Abstract: ASYMMETRIC TOTAL SYNTHESIS OF 11α-HYDROXYPROGESTERONE VIA A BIOMIMETIC POLYENE CYCLIZATION

1978 ◽  
Vol 9 (12) ◽  
Author(s):  
W. S. JOHNSON ◽  
R. S. BRINKMEYER ◽  
V. M. KAPOOR ◽  
T. M. YARNELL
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

Asymmetric Total Synthesis of Norzoanthamine

2021 ◽  
Author(s):  
Zhengyuan Xin ◽  
Hui Wang ◽  
Haibing He ◽  
Xiaoli Zhao ◽  
Shuanhu Gao
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

scholarly journals Asymmetric Total Synthesis of Hetiamacins A–F

ACS Omega ◽  
2021 ◽  
Vol 6 (12) ◽  
pp. 8239-8245
Author(s):  
Gang Wu ◽  
Ting Wang ◽  
Zhongke Jiang ◽  
Shaowei Liu ◽  
Chenghang Sun
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis

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
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