Total Synthesis of (±)-Trachyspic Acid and Determination of the Relative Configuration

2003 ◽  
Vol 5 (6) ◽  
pp. 857-859 ◽  
Author(s):  
Kanako Hirai ◽  
Hidenori Ooi ◽  
Tomoyuki Esumi ◽  
Yoshiharu Iwabuchi ◽  
Susumi Hatakeyama
Keyword(s):  
Total Synthesis ◽  
Relative Configuration

scholarly journals Synthesis of eunicellane-type bicycles embedding a 1,3-cyclohexadiene moiety

2018 ◽  
Vol 14 ◽  
pp. 2461-2467 ◽  
Author(s):  
Alex Frichert ◽  
Peter G Jones ◽  
Thomas Lindel
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Selective Reduction ◽  
Relative Configuration ◽  
Pinacol Coupling ◽  
Low Valent ◽  
Limonene Oxide

The first synthesis of diterpenoid eunicellane skeletons incorporating a 1,3-cyclohexadiene moiety is presented. Key step is a low-valent titanium-induced pinacol cyclization that proved to be perfectly diastereoselective. Determination of the relative configuration of the diol was aided by the conversion to the diastereomer by oxidation and reduction. Conformational analysis of some of the resulting diols obtained under McMurry conditions was complicated by the presence of several conformers of similar energy. The pinacol coupling appears to start at the ketone, as indicated by the selective reduction of non-cyclizing cyclohexane systems that were synthesized from limonene oxide. The title compounds and their synthetic precursors are prone to aromatization on contact with air oxygen. Attempted synthesis of cyclohexene-containing eunicellane bicycles by elimination of water from tertiary alkynyl carbinols afforded novel allene systems. Our study may be of help towards the total synthesis of solenopodin or klysimplexin derivatives.

Total synthesis of melleumins A and B and their analogs: Determination of stereochemistry and Wnt signal inhibitory activity

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
M Ishibashi ◽  
S Hanazawa ◽  
Y Uchino ◽  
X Li ◽  
MA Arai
Keyword(s):  
Total Synthesis ◽  
Inhibitory Activity ◽  
Wnt Signal

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

Determination of Relative Configuration in Organic Compounds by NMR Spectroscopy and Computational Methods

ChemInform ◽  
2007 ◽  
Vol 38 (50) ◽  
Author(s):  
Giuseppe Bifulco ◽  
Paolo Dambruoso ◽  
Luigi Gomez-Paloma ◽  
Raffaele Riccio
Keyword(s):  
Nmr Spectroscopy ◽  
Organic Compounds ◽  
Computational Methods ◽  
Relative Configuration

Determination of the Relative Configuration of β-Amino Acid Esters Based on Residual Dipolar Couplings

2015 ◽  
Vol 2015 (31) ◽  
pp. 6801-6805 ◽  
Author(s):  
Thomas Niklas ◽  
Christian Steinmetzger ◽  
Weiping Liu ◽  
Daniel Zell ◽  
Dietmar Stalke ◽  
...  
Keyword(s):  
Amino Acid ◽  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Amino Acid Esters ◽  
Relative Configuration ◽  
Acid Esters
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