Total Synthesis of the Meroterpenoid Manginoid A as Fueled by a Challenging Pinacol Coupling and Bicycle‐forming Etherification

2021 ◽  
Author(s):  
Yu-An Zhang ◽  
Amanda Milkovits ◽  
Valay Agarawal ◽  
Cooper A Taylor ◽  
Scott A Snyder
Keyword(s):  
Total Synthesis ◽  
Pinacol Coupling

Total synthesis of (.+-.)-crassin by titanium-induced pinacol coupling

1989 ◽  
Vol 111 (24) ◽  
pp. 8928-8929 ◽  
Author(s):  
John E. McMurry ◽  
R. G. Dushin
Keyword(s):  
Total Synthesis ◽  
Pinacol Coupling

Periplanone total synthesis via intramolecular pinacol coupling

1994 ◽  
Vol 35 (26) ◽  
pp. 4505-4508 ◽  
Author(s):  
John E. McMurry ◽  
Nathan O. Siemers
Keyword(s):  
Total Synthesis ◽  
Pinacol Coupling

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.

ChemInform Abstract: Periplanone Total Synthesis via Intramolecular Pinacol Coupling.

ChemInform ◽  
2010 ◽  
Vol 25 (46) ◽  
pp. no-no
Author(s):  
J. E. MCMURRY ◽  
N. O. SIEMERS
Keyword(s):  
Total Synthesis ◽  
Pinacol Coupling

Total Synthesis of the Meroterpenoid Manginoid A as Fueled by a Challenging Pinacol Coupling and Bicycle‐forming Etherification

2021 ◽  
Author(s):  
Yu‐An Zhang ◽  
Amanda Milkovits ◽  
Valay Agarawal ◽  
Cooper A. Taylor ◽  
Scott A. Snyder
Keyword(s):  
Total Synthesis ◽  
Pinacol Coupling

Total synthesis of Δ9(12)-capnellene-8α,10α-diol

1982 ◽  
Vol 23 (52) ◽  
pp. 5471-5474
Author(s):  
G Pattenden
Keyword(s):  
Total Synthesis

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
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