Total synthesis of 14β-fluorosteroids via a transannular Diels–Alder reaction

2006 ◽  
Vol 84 (1) ◽  
pp. 29-48 ◽  
Author(s):  
Sylvie Beaubien ◽  
Pierre Deslongchamps
Keyword(s):  
Cardiovascular Diseases ◽  
Total Synthesis ◽  
Key Words ◽  
Inhibitory Activity ◽  
Alder Reaction ◽  
Diels Alder ◽  
New Class ◽  
Diels Alder Reaction

14β-Fluorosteroids 3 and 4 were synthesized to give a new class of unnatural cardenolides. The total synthesis of racemic 14β-fluorosteroids was accomplished using a highly diastereoselective transannular Diels–Alder reaction on a trans-cis-cis macrocyclic triene. The α-fluoro analog 4 provided a comparable inhibitory activity to natural digitoxigenin 1.Key words: fluorosteroid, bioisostere, cardiovascular diseases, transannular Diels–Alder reaction (TADA), macrocyclization.

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
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