138665-79-9

Upstream product

• 108686-36-8 tricyclo<6.3.0.0^2,6>undec-2(6)-en-7-one 
• 138622-57-8 decahydro<3aα,3bβ,6aβ,7aα>-7H-cyclopentapentalen-7-ol 
• 58866-22-1 α,α'-dicyclopentenyl ketone 
• 96-22-0 pentan-3-one 
• 61617-58-1 tricyclo<6.3.0.0^2,7>undecan-3-one 
• 142-29-0 cyclopentene 

Relevant academic research and scientific papers

Ionic hydrogenation of oxyallyl intermediates: The reductive nazarov cyclization

Cyclization of tri- and tetrasubstituted dienones 1 under Lewis acidic conditions in the presence of triethylsilane led to formation of either silyl enol ethers 6 or cyclopentanones 7 in good to excellent yields, depending on work-up conditions. The proposed mechanism involves initial Nazarov cyclization to give oxyallyl intermediates 5, which are intercepted via intermolecular transfer of hydride. The reactions proceeded cleanly with as little as 2 equiv. of silane and in most cases catalytic amounts of Lewis acid could be used. Trapping with Et3SiD occurs at the less substituted terminus in unsymmetrical cases. (C) 2000 Elsevier Science Ltd.

The reductive Nazarov cyclization

Tri- and tetrasubstituted 1,4-dien-3-ones 1 were treated with Lewis acid in the presence of triethylsilane, furnishing either silyl enol ethers 4 or cyclopentanones 5 in good yields, depending upon work-up conditions. This reaction is presumed to occur th

Cyclobutane ring expansion in tricyclo2,7>undecan-3-ol. Potential application in the synthesis of triquinane and cyclopentacyclooctane derivatives

The acid catalysed rearrangement of tricyclo2,7>undecan-3-ol (2) gives 2,3,3b,4,5,6,6a,7-octahydro-1H-cyclopentapentalene (3) as the major product which is converted to decahydro-1H-cyclopentacyclooctane-4,8-dione (8).The other products of rearrangement are cis-anti-cis- and cis-syn-cis-decahydro-7H-cyclopentapentalen-7-ols (4 and 5), decahydro-9(endo)hydroxy- and decahydro-9(exo)hydroxy-4,8-methanoazulenes (6 and 7).

Synthesis of a New Ketone and Alcohol with C2 Symmetry; (S,S,S,S) Tricyclo3,7>undecan-2-one and (S,S,S,S) Tricyclo3,7>undecan-2-ol

Dissolving metal reduction of known enone 5 affords predominantly the racemic form of the title ketone (3) whereas catalytic reduction gives the meso isomer 6.Neither ketone 3 nor alcohol 4 could be satisfactorily resolved.Asymmetric synthesis of (-)-3 and (+)-4 (ee=91percent) was effected from ketone (+)-13.