Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation

Tetrahedron ◽  
1996 ◽  
Vol 52 (11) ◽  
pp. 3921-3932 ◽  
Author(s):  
Nobuo Kato ◽  
Hiroaki Okamoto ◽  
Hitoshi Takeshita
Keyword(s):  
Total Synthesis ◽  
Leaf Growth ◽  
Membered Ring ◽  
Optically Active ◽  
Ring Formation ◽  
Fungal Metabolite ◽  
Ene Reaction ◽  
Growth Activity

ChemInform Abstract: Total Synthesis of (-)-Cotylenol, a Fungal Metabolite Having Leaf Growth Activity.

ChemInform ◽  
2010 ◽  
Vol 26 (22) ◽  
pp. no-no
Author(s):  
H. OKAMOTO ◽  
H. ARITA ◽  
N. KATO ◽  
H. TAKESHITA
Keyword(s):  
Total Synthesis ◽  
Leaf Growth ◽  
Fungal Metabolite ◽  
Growth Activity

Total Synthesis of (−)-Cotylenol, a Fungal Metabolite Having a Leaf Growth Activity

1994 ◽  
Vol 23 (12) ◽  
pp. 2335-2338 ◽  
Author(s):  
Hiroaki Okamoto ◽  
Hiroaki Arita ◽  
Nobuo Kato ◽  
Hitoshi Takeshita
Keyword(s):  
Total Synthesis ◽  
Leaf Growth ◽  
Fungal Metabolite ◽  
Growth Activity

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.

ChemInform Abstract: Studies Towards the Total Synthesis of Solanoeclepin A: Synthesis of the 7-Oxabicyclo[2.2.1]heptane Moiety and Attempted Seven-Membered Ring Formation.

ChemInform ◽  
2010 ◽  
Vol 33 (47) ◽  
pp. no-no
Author(s):  
Jorg C. J. Benningshof ◽  
Richard H. Blaauw ◽  
Angeline E. van Ginkel ◽  
Jan H. van Maarseveen ◽  
Flories P. J. T. Rutjes ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Membered Ring ◽  
Ring Formation

Studies towards the total synthesis of solanoeclepin A: synthesis of the 7-oxabicyclo[2.2.1]heptane moiety and attempted seven-membered ring formation

2002 ◽  
pp. 1693-1700 ◽  
Author(s):  
Jorg C. J. Benningshof ◽  
Richard H. Blaauw ◽  
Angeline E. van Ginkel ◽  
Jan H. van Maarseveen ◽  
Floris P. J. T. Rutjes ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Membered Ring ◽  
Ring Formation
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