Formal synthesis of englerin A utilizing regio- and diastereoselective [4+3] cycloaddition

2017 ◽  
Vol 71 (2) ◽  
pp. 257-262 ◽  
Author(s):  
Shuichi Hagihara ◽  
Kengo Hanaya ◽  
Takeshi Sugai ◽  
Mitsuru Shoji
Keyword(s):  
Formal Synthesis ◽  
Englerin A

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

Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (−)-Englerin A

2017 ◽  
Vol 19 (19) ◽  
pp. 5142-5145 ◽  
Author(s):  
Keisuke Morisaki ◽  
Yusuke Sasano ◽  
Takahiro Koseki ◽  
Takuro Shibuta ◽  
Naoki Kanoh ◽  
...  
Keyword(s):  
Building Blocks ◽  
Nazarov Cyclization ◽  
Formal Synthesis ◽  
Englerin A

ChemInform Abstract: Enantioselective Formal Synthesis of (-)-Englerin A (V) via a Rh-Catalyzed [4 + 3] Cycloaddition Reaction.

ChemInform ◽  
2010 ◽  
Vol 41 (51) ◽  
pp. no-no
Author(s):  
Jing Xu ◽  
Eduardo J. E. Caro-Diaz ◽  
Emmanuel A. Theodorakis
Keyword(s):  
Cycloaddition Reaction ◽  
Formal Synthesis ◽  
Englerin A

scholarly journals Enantioselective Formal Synthesis of (−)-Englerin A via a Rh-Catalyzed [4 + 3] Cycloaddition Reaction

2010 ◽  
Vol 12 (16) ◽  
pp. 3708-3711 ◽  
Author(s):  
Jing Xu ◽  
Eduardo J. E. Caro-Diaz ◽  
Emmanuel A. Theodorakis
Keyword(s):  
Cycloaddition Reaction ◽  
Formal Synthesis ◽  
Englerin A

scholarly journals Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction

Synlett ◽  
2012 ◽  
Vol 23 (08) ◽  
pp. 2266-2266
Author(s):  
Bing-Feng Sun ◽  
Guo-Qiang Lin ◽  
Jin-Yi Xu ◽  
Chao-Lei Wang ◽  
Shu-Guang Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Formal Synthesis ◽  
Englerin A

Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction

Synlett ◽  
2011 ◽  
Vol 2012 (02) ◽  
pp. 263-266 ◽  
Author(s):  
Bing-Feng Sun ◽  
Guo-Qiang Lin ◽  
Jin-Yi Xu ◽  
Chao-Lei Wang ◽  
Shu-Guang Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cycloaddition Reaction ◽  
Formal Synthesis ◽  
Englerin A

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.

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