Total Synthesis of Periplanone-B Via Intramolecular Diels-Alder Reaction with Furan-Diene and Allene-Dienophile

2010 ◽  
Vol 103 (7-8) ◽  
pp. 433-443 ◽  
Author(s):  
Tom De Geyter ◽  
Serge Cauwberghs ◽  
Pierre J. De Clercq
2017 ◽  
Vol 19 (3) ◽  
pp. 429-431 ◽  
Author(s):  
Tian-Ze Li ◽  
Chang-An Geng ◽  
Xiu-Juan Yin ◽  
Tong-Hua Yang ◽  
Xing-Long Chen ◽  
...  

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura

1979 ◽  
Vol 57 (24) ◽  
pp. 3354-3356 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Leonard Allain ◽  
Robert A. Dickinson ◽  
Peter S. White ◽  
Zdenek Valenta

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.


1996 ◽  
pp. 225-226 ◽  
Author(s):  
Goh Matsuo ◽  
Yuko Miki ◽  
Masaya Nakata ◽  
Shuichi Matsumura ◽  
Kazunobu Toshima

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