23963-16-8

Upstream product

• 244628-36-2 (2S,3S,3aS,4aS,5R,8S,8aR,2'R,1E)-2-(2'phenylmethyloxy-tridecyl)-3-(1-hexenyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole 
• 2767-84-2 Camphorquinone 
• 1111092-21-7 (1R,2S,5R,8S,1'S)-5-(1'-hydroxy-o-chlorobenzyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 1111092-20-6 (1R,2S,5R,8S,1'S)-5-(1'-hydroxy-o-fluorobenzyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 1111092-19-3 (1R,2S,5R,8S,1'S)-5-(1'-hydroxybenzyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 1111092-18-2 (1R,2S,5R,8S,1'R)-5-(1'-hydroxy-1'-cyclohexylmethyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 1111092-16-0 (1R,2S,5R,8S,1'R)-5-(1'-hydroxy-iso-butyl)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 
• 100-39-0 benzyl bromide 
• 110259-71-7 (1R,4S)-3,3-Dimethoxy-bornan-2-one 
• 10334-26-6 (R)-camphorquinone 

Downstream Products

• 77078-84-3 (+)-(1R,2S,3S,4S)-3-endo-(4-Methoxyphenyl)-2-exo,3-exo-bornandiol 
• 77078-82-1 (+)-(1R,2S,3S,4S)-3-endo-(2,4,6-Trimethylphenyl)-2-exo,3-exo-bornandiol 
• 77078-83-2 (+)-(1R,2S,3S,4S)-3-endo-(2-Methoxyphenyl)-2-exo,3-exo-bornandiol 
• 77078-79-6 (-)-(1R,2S,3R,4S)-3-endo-Benzyl-2-exo,3-exo-bornandiol 
• 67814-35-1 (+)-(1R,2S,3S,4S)-1,7,7-trimethyl-3-phenylbicyclo[2.2.1]heptane-2,3-diol 
• 77122-66-8 (1R,2S,3R,4S)-1,7,7-Trimethyl-3-phenyl-bicyclo[2.2.1]heptane-2,3-diol 
• 422570-19-2 (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 422570-14-7 (1R,2S,4S)-benzyloxycarbonylaminoacetic acid 1,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-yl ester 
• 77118-84-4 (-)-(1R,2S,3R,4S)-3-endo-<(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-oxazolin-2-ylmethyl>-2-exo,3-exo-bornandiol 

Relevant academic research and scientific papers

Diastereo- And enantioselective synthesis of β-Hydroxy-α-amino acids: Application to the synthesis of a key intermediate for lactacystin

The development of a highly efficient and stereoselective methodology for the preparation of β-hydroxy-α- amino acids is described. Nucleophilic addition of enolates of tricyclic iminolactones 1a and 1b to aldehydes in the presence of 6 equiv of lithium chloride in THF at -78 °C leads to aldol adducts in good yield (63-86%) and high diastereoselectivity (up to >25:1 dr). Subsequently, hydrolysis of the aldol adducts under acidic conditions leads to the corresponding β-hydroxy-a-amino acids in good yields (up to 83%) and excellent enantiomeric excesses (99% ee) with good recovery yields of the chiral auxiliaries 6 and 7. This methodology was applied to the facile synthesis of the key intermediate for lactacystin along with several isomers.

Biotransformation of (+)- and (-)-camphorquinones by plant cultured cells

Biotransformation of (+)- and (-)-camphorquinones with suspension plant cultured cells of Nicotiana tabacum and Catharanthus roseus was investigated. It was found that the plant cultured cells of N. tabacum and C. roseus reduce stereoselectively the carbonyl group of (+)- and (-)-camphorquinones to the corresponding α-keto alcohols.

Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

Formula presented A [2+3] cycloaddition of camphor-derived oxazoline N-oxide to α,β-unsaturated ester afforded adduct 8. Tetrahydrolipstatin 1 was prepared from this compound in a nine-step sequence of reactions.

Minor Products in Photoreactions of α-Diketones with Arenes. Abstraction of Hydroxylic Hydrogen by Triplet Carbonyl

Photochemical reactions of cyclic saturated α-diketones in toluene or p-xylene produce 1:1 adducts as major products and smaller amounts of reduced diketone and bibenzyls, as expected from previous work.In addition, reaction of BOD gave 2percent of the decarbonylation product, p-methylbenzyl cyclohexyl ketone; reaction of camphorquinone gave a mixture of decarbonylation products (10percent total) including saturated and unsaturated monoketones.These compounds were secondary products arising from reaction of photoexcited diketone with the initially formed adducts; quenching andsensitization studies showed that triplet states of α-diketones were involved in both primary and secondary reactions.The decarbonylation products were also formed by reaction of benzophenone triplets or of tert-butoxy radicals with adducts.Deuterium labeling of the adducts was employed to demonstrate that the decarbonylation process involves abstraction of hydroxylic hydrogen.

An Improved Synthesis of (-)-(1R,2S,3R,4S)-2-Benzyloxy-3-bornanol (12) on a Preparative Scale

A method is described for the separation of (-)-(1R,2S,3R,4S)-2-benzyloxy-3-bornanol 12 in preparative amounts in the form of its formate 17 from the accompanying diastereomers 13-15.

Reduction by a Model of NAD(P)H. 32. Stereoselective Reduction of Camphoroquinone by a Chiral NAD(P)H Model

(+)-, (-)-, and racemic camphoroquinones (CQ) were reduced by each of four NAD(P)H-models such as N-(α-methylbenzyl)-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide (Me2PNPH) in the presence of magnesium ion in acetonitrile with a view to elucidating the intermolecular arrangement in the transition state for asymmetric reduction.Partial rate factors for each attacking mode were calculated.Electronegative substituents in the substrate prefer to facing the carbamoyl group in Me2PNPH, which is the most important factor determining the stereochemical course of the reduction. 1-Methyl group in CQ has a tendency to interfere with the dihydropyridine moiety in Me2PNPH approaching the C2-carbonyl group in CQ.This interference is more important for the selectivity than the intrinsic exo/endo reactivity difference.