Total synthesis of (.+-.)-nitramine. Development of a ketene equivalent in the ene reaction

1984 ◽  
Vol 49 (10) ◽  
pp. 1688-1691 ◽  
Author(s):  
Barry B. Snider ◽  
Claudia P. Cartaya-Marin
Keyword(s):  
Total Synthesis ◽  
Ene Reaction

ChemInform Abstract: Total Synthesis of (+)-Arteanniun M Using the Tandem Oxy-Cope/Ene Reaction.

ChemInform ◽  
2010 ◽  
Vol 32 (52) ◽  
pp. no-no
Author(s):  
Louis Barriault ◽  
Daniel H. Deon
Keyword(s):  
Total Synthesis ◽  
Ene Reaction

ChemInform Abstract: Total Synthesis of the Unusual Marine Alkaloid (-)-Papuamine Utilizing a Novel Imino Ene Reaction.

ChemInform ◽  
2010 ◽  
Vol 27 (11) ◽  
pp. no-no
Author(s):  
R. M. BORZILLERI ◽  
S. M. WEINREB ◽  
M. PARVEZ
Keyword(s):  
Total Synthesis ◽  
Ene Reaction ◽  
Marine Alkaloid

Total Synthesis of (+)-Arteanniun M Using the Tandem Oxy-Cope/Ene Reaction

2001 ◽  
Vol 3 (12) ◽  
pp. 1925-1927 ◽  
Author(s):  
Louis Barriault ◽  
Daniel H. Deon
Keyword(s):  
Total Synthesis ◽  
Ene Reaction

Synthesis of 8,14-Secosteroids from (S)-(+)-Carvone

2000 ◽  
Vol 65 (7) ◽  
pp. 1173-1182 ◽  
Author(s):  
Anna I. Kotyatkina ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
Aede de Groot
Keyword(s):  
Total Synthesis ◽  
Membered Ring ◽  
Reductive Cleavage ◽  
Nitrile Oxide ◽  
Side Chain ◽  
Ene Reaction ◽  
Nitrile Oxides ◽  
Cyclic Enones ◽  
Derivatives Of ◽  
Ab Ring

A total synthesis of functionalised 8,14-seco steroids with five- and six-membered D rings is described. The synthesis is based on the transformation of (S)-carvone into a steroidal AB ring moiety with a side chain at C-9 that allowed the creation of a nitrile oxide at this position. The nitrile oxides were coupled with cyclic enones or enol derivatives of 1,3-diketones, and reductive cleavage of the obtained cycloadducts gave the desired products. The formation of a twelve-membered ring compound was observed in cycloaddition of one of the nitrile oxides with cyclopentenone as the result of an intramolecular ene-reaction followed by retroaldol reaction.

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