Total synthesis of mycophenolic acid

1997 ◽  
Vol 75 (6) ◽  
pp. 641-645 ◽  
Author(s):  
Ricardo A. de la Cruz ◽  
Francisco X. Talamás ◽  
Alfredo Vázquez ◽  
Joseph M. Muchowski
Keyword(s):  
Total Synthesis ◽  
Mycophenolic Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Side Chain ◽  
Diels Alder Reaction

A total synthesis of mycophenolic acid is reported. Diels–Alder reaction of [5-methoxy-3-(1-methoxypropenyl)-4,5-dihydrofuran-2-yloxy]-trimethylsilane with 3-benzenesulfinyl-5H-furan-2-one afforded the hexasubstituted nucleus. The side chain was constructed from the unveiled aldehyde. Keywords: mycophenolic acid, Diels–Alder reaction, pentasubstituted diene.

Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction

2017 ◽  
Vol 19 (3) ◽  
pp. 429-431 ◽  
Author(s):  
Tian-Ze Li ◽  
Chang-An Geng ◽  
Xiu-Juan Yin ◽  
Tong-Hua Yang ◽  
Xing-Long Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione

1979 ◽  
Vol 57 (24) ◽  
pp. 3354-3356 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Leonard Allain ◽  
Robert A. Dickinson ◽  
Peter S. White ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Allylic Alcohol ◽  
Diels Alder Reaction

A total synthesis of (±)-5β,8α- androst-9(11)-ene-3,17-dione is described. The key step is a ring C forming SnCl4-catalyzed Diels–Alder reaction in which the geometry of the diene controls syn–anti stereochemistry while the catalyst guides the addition to the desired endo orientation. A preparation of ethyl E-2-methyl-4-oxo-2-butenoate and the dehydration of a tertiary allylic alcohol by the pyrolysis of the corresponding tosyl carbamate are also described.

Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels–Alder reaction of C-glycosyl juglone

1996 ◽  
pp. 225-226 ◽  
Author(s):  
Goh Matsuo ◽  
Yuko Miki ◽  
Masaya Nakata ◽  
Shuichi Matsumura ◽  
Kazunobu Toshima
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Asymmetric Total Synthesis of (+)-Coprophilin

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1301-1306 ◽  
Author(s):  
Isamu Shiina ◽  
Yuma Umezaki ◽  
Takatsugu Murata ◽  
Kyohei Suzuki ◽  
Takayuki Tonoi
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Anticoccidial Agent

In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure.

Sign in / Sign up

Export Citation Format

Share Document