Concise Syntheses of Strychnine and Englerin A: the Power of Reductive Cyclizations Triggered by Samarium Iodide

2011 ◽  
Vol 50 (34) ◽  
pp. 7737-7739 ◽  
Author(s):  
Michal Szostak ◽  
David J. Procter
Keyword(s):  
Englerin A ◽  
Samarium Iodide ◽  
Reductive Cyclizations

Microbe Engineering of Guaia-6,10(14)-diene as a Building Block for the Semisynthetic Production of Plant-Derived (−)-Englerin A

2019 ◽  
Author(s):  
Thomas Siemon ◽  
Zhangqian Wang ◽  
Guangkai Bian ◽  
Tobias Seitz ◽  
Ziling Ye ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Saccharomyces Cerevisiae ◽  
Synthetic Biology ◽  
Chemical Synthesis ◽  
Building Block ◽  
Transient Receptor Potential ◽  
Receptor Potential ◽  
Economical Method ◽  
Englerin A ◽  
Transient Receptor

Herein, we report the semisynthetic production of the potent transient receptor potential canonical (TRPC) channel agonist (−)-englerin A (EA), using guaia-6,10(14)-diene as the starting material. Guaia-6,10(14)-diene was systematically engineered in Escherichia coli and Saccharomyces cerevisiae using the CRISPR/Cas9 system and produced with high titers. This provided us the opportunity to execute a concise chemical synthesis of EA and the two related guaianes (−)-oxyphyllol and (+)-orientalol E. The potentially scalable approach combines the advantages of synthetic biology and chemical synthesis and provides an efficient and economical method for producing EA as well as its analogs.

Microbe Engineering of Guaia-6,10(14)-diene as a Building Block for the Semisynthetic Production of Plant-Derived (−)-Englerin A

2019 ◽  
Author(s):  
Thomas Siemon ◽  
Zhangqian Wang ◽  
Guangkai Bian ◽  
Tobias Seitz ◽  
Ziling Ye ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Saccharomyces Cerevisiae ◽  
Synthetic Biology ◽  
Chemical Synthesis ◽  
Building Block ◽  
Transient Receptor Potential ◽  
Receptor Potential ◽  
Economical Method ◽  
Englerin A ◽  
Transient Receptor

Herein, we report the semisynthetic production of the potent transient receptor potential canonical (TRPC) channel agonist (−)-englerin A (EA), using guaia-6,10(14)-diene as the starting material. Guaia-6,10(14)-diene was systematically engineered in Escherichia coli and Saccharomyces cerevisiae using the CRISPR/Cas9 system and produced with high titers. This provided us the opportunity to execute a concise chemical synthesis of EA and the two related guaianes (−)-oxyphyllol and (+)-orientalol E. The potentially scalable approach combines the advantages of synthetic biology and chemical synthesis and provides an efficient and economical method for producing EA as well as its analogs.

scholarly journals A concise enantioselective synthesis of the guaiane sesquiterpene (−)-oxyphyllol

2013 ◽  
Vol 9 ◽  
pp. 2028-2032 ◽  
Author(s):  
Martin Zahel ◽  
Peter Metz
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Englerin A ◽  
Epoxide Opening

(−)-Oxyphyllol was prepared in only 4 steps from an epoxy enone that already served as an intermediate for the total synthesis of the anticancer guaiane (−)-englerin A. A regio- and diastereoselective Co(II)-catalyzed hydration of the olefin and a transannular epoxide opening were used as the key reactions.

scholarly journals Formal Synthesis of (−)-Englerin A and Cytotoxicity Studies of Truncated Englerins

2012 ◽  
Vol 7 (5) ◽  
pp. 1052-1060 ◽  
Author(s):  
Jing Xu ◽  
Eduardo J. E. Caro-Diaz ◽  
Ayse Batova ◽  
Steven D. E. Sullivan ◽  
Emmanuel A. Theodorakis
Keyword(s):  
Formal Synthesis ◽  
Englerin A ◽  
Cytotoxicity Studies

Total Synthesis of Englerin A

2010 ◽  
Vol 132 (23) ◽  
pp. 8219-8222 ◽  
Author(s):  
K. C. Nicolaou ◽  
Qiang Kang ◽  
Sin Yee Ng ◽  
David Y.-K. Chen
Keyword(s):  
Total Synthesis ◽  
Englerin A

Synthesis of (–)-Englerin A

Synfacts ◽  
2016 ◽  
Vol 13 (01) ◽  
pp. 0012-0012
Keyword(s):  
Englerin A
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