A General Access to Zaragozic Acids: Total Synthesis and Structure Elucidation of Zaragozic Acid D and Formal Syntheses of Zaragozic Acids A and C

2011 ◽  
Vol 17 (12) ◽  
pp. 3335-3337 ◽  
Author(s):  
Yuzhou Wang ◽  
Peter Metz
Keyword(s):  
Total Synthesis ◽  
Structure Elucidation ◽  
Zaragozic Acids ◽  
Zaragozic Acid

ChemInform Abstract: Total Synthesis and Structure Elucidation of (.+-.)-Triumphalone and (.+-.)-Isotriumphalone.

ChemInform ◽  
2015 ◽  
Vol 46 (22) ◽  
pp. no-no
Author(s):  
Eiji Nishimura ◽  
Yasufumi Ohfune ◽  
Tetsuro Shinada
Keyword(s):  
Total Synthesis ◽  
Structure Elucidation

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition Strategy

2003 ◽  
Vol 115 (43) ◽  
pp. 5509-5513 ◽  
Author(s):  
Seiichi Nakamura ◽  
Yuuki Hirata ◽  
Takahiro Kurosaki ◽  
Masahiro Anada ◽  
Osamu Kataoka ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Squalene Synthase ◽  
Carbonyl Ylide ◽  
Zaragozic Acid ◽  
Synthase Inhibitor ◽  
Squalene Synthase Inhibitor ◽  
Zaragozic Acid C

Total Synthesis Guided Structure Elucidation of (+)‐Psychotetramine

2011 ◽  
Vol 123 (12) ◽  
pp. 2768-2771 ◽  
Author(s):  
Klement Foo ◽  
Timothy Newhouse ◽  
Ikue Mori ◽  
Hiromitsu Takayama ◽  
Phil S. Baran
Keyword(s):  
Total Synthesis ◽  
Structure Elucidation

Structure Elucidation and Total Synthesis of Kulkenon

2014 ◽  
Vol 53 (7) ◽  
pp. 1795-1798 ◽  
Author(s):  
Gerrit Symkenberg ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Structure Elucidation

Structure elucidation of hypocreolide A by enantioselective total synthesis

2010 ◽  
Vol 8 (9) ◽  
pp. 2123 ◽  
Author(s):  
Katharina Götz ◽  
Johannes C. Liermann ◽  
Eckhard Thines ◽  
Heidrun Anke ◽  
Till Opatz
Keyword(s):  
Total Synthesis ◽  
Structure Elucidation ◽  
Enantioselective Total Synthesis

Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C by a Carbonyl Ylide Cycloaddition Strategy.

ChemInform ◽  
2004 ◽  
Vol 35 (11) ◽  
Author(s):  
Seiichi Nakamura ◽  
Yuuki Hirata ◽  
Takahiro Kurosaki ◽  
Masahiro Anada ◽  
Osamu Kataoka ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Squalene Synthase ◽  
Carbonyl Ylide ◽  
Zaragozic Acid ◽  
Synthase Inhibitor ◽  
Squalene Synthase Inhibitor ◽  
Zaragozic Acid C
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