164414-40-8

Upstream product

• 164414-39-5 acetic acid (1R,4S)-(-)-(tert-butyldimethylsiloxy)cyclohex-2-enyl ester 
• 1165952-91-9 cyclohexa-1,3-diene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 132617-05-1 acetic acid (1S,4R)-(-)-4-hydroxycyclohex-2-enyl ester 

Downstream Products

• 164577-42-8 <(4R)-(+)-tert-Butoxydimethylsiloxy>-2-cyclohexen-1-on 
• 189082-04-0 tert-Butyl-((1R,4R)-4-chloro-cyclohex-2-enyloxy)-dimethyl-silane 
• 852546-56-6 (1S,4R,7R,8R)-8-(4-Methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-one 
• 852546-59-9 (1S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-one 
• 852546-66-8 2,2-Dimethyl-propionic acid (1S,2R,3R,4S,7R)-5-oxo-7-p-tolyloxythiocarbonyloxy-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-ylmethyl ester 
• 852546-71-5 (1R,2R)-1-[(1S,2R,3R,4R,7S)-7-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-7-hydroxy-3-(4-methoxy-benzyloxymethyl)-bicyclo[2.2.2]oct-5-en-2-yl]-propane-1,2-diol 
• 852546-57-7 (1S,2S,4R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-5-en-2-ol 
• 852546-69-1 (1S,2S,4S,5R,7R,8R)-2-[(E)-2-(Dimethyl-phenyl-silanyl)-vinyl]-8-(4-methoxy-benzyloxymethyl)-7-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octane-2,5-diol 
• 852546-60-2 (1S,2S,4S,5R,6R,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-(4-methoxy-benzyloxymethyl)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]octan-2-ol 
• 852546-70-4 Thiocarbonic acid O-[(1S,2R,4S,5S,7R,8R)-5-[(E)-2-(dimethyl-phenyl-silanyl)-vinyl]-5-hydroxy-7-(4-methoxy-benzyloxymethyl)-8-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.2]oct-2-yl] ester O-p-tolyl ester 
• 122052-53-3 (2R,3R,4R)-(-)-4-(tert-butyldimethylsiloxy)-2,3-dimethylcyclohexanone 
• 189081-95-6 Acetic acid (1R,4R)-4-benzylamino-cyclohex-2-enyl ester 
• 189081-92-3 Acetic acid (1R,4R)-4-diethylamino-cyclohex-2-enyl ester 
• 189081-97-8 (1R,4R)-(+)-1-Acetoxy-4-chlorocyclohex-2-ene 

Relevant academic research and scientific papers

Synthetic studies toward the construction of the cis-decalin portion of superstolides A and B. Application of a sequential double Michael reaction and an anionic oxy-Cope rearrangement

(Chemical Equation Presented) A highly convergent strategy for the asymmetric synthesis of the cis-decalin portion of the antitumor macrolide superstolide A was developed. The key reactions in our approach involve a sequential double Michael reaction and

Palladium-catalysed enantiodivergent synthesis of cis- and trans-4-aminocyclohex-2-enols

Enantiomerically pure cis- and trans-4-aminocyclohex-2-enols are prepared from cyclohexa-1,3-diene via (-)-cis-(1R,4S)-4-acetoxycyclohex-2-enol (-)-2a using palladium(0) chemistry. Benzylamine and diethylamine are tested in the Pd0-catalysed allylic amination reactions. Since acetate is too slow as a leaving group and gave considerable amounts of side products, a number of leaving groups have been investigated. Of these phosphinate and 2,4-dichlorobenzoate are excellent leaving groups and result in efficient and highly stereoselective reactions; chloride as allylic leaving group also gives good results. By variation of the leaving group and proper choice of the protecting group it is possible to synthesise all four stereoisomers of 4-aminocyclohex-2-enol in good yield and high enantiomeric excess.

The total synthesis of (+)-petasin and (+)-isopetasin

Petasin 1 and isopetasin 2, anti-inflammatory and analgesic components of the butterbur (Petasites hybridus), were prepared for the first time in a short and enantioselective synthesis. The key steps were a Michael addition/alkylation (7 → 8), an enamine alkylation to give 9 and a cyclization with N-phenyliminoketenylidenetriphenylphosphorane 11 (10 → 15).

Synthese der Pestwurzinhaltsstoffe (+)-Petasin und (+)-Isopetasin

The first total synthesis of optically active petasine 1 and isopetasine 2 succeeded by applying an annelation reaction, based on the reaction of cyclic δ-ketocarboxylic acids with N-phenyliminoketenylidenetriphenylphosphorane. 1 and 2 are biologically ac