171523-67-4

Upstream product

• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 
• 182219-57-4 methyl (+)-(SR)-3,5-dioxo-6-(p-toluenesulfinyl)hexanoate 
• 171523-66-3 (+)-(R)-Methyl 3,5-dioxo-6-(p-tolylsulfinyl)hexanoate 

Downstream Products

• 191854-41-8 (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate 
• 171523-69-6 (+)-<3(R),5(S),S(R)>-Methyl syn-3,5-(isopropylidenedioxy)-6-(p-tolylsulfinyl)hexanoate 
• 263369-09-1 3'-methyl-2'-butenyl (+)-(5S,7R,13R,2E,10E)-13-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoate 
• 263369-08-0 3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate 
• 263369-07-9 methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate 
• 263369-05-7 (+)-(3R,5R)-3-(tert-butyldiphenylsilyloxy)-5-hexanolide 
• 263369-06-8 (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol 
• 50376-40-4 (-)-colletol 

Relevant academic research and scientific papers

Enantioselective synthesis of a bicyclic ketal induced by chiral sulfoxides: (-)-(1R,3R,5S)-endo-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane

The bicyclic ketal, (-)-(1R,3R,5S)-1,3-dimethyl-2,9-dioxabicyclo-[3,3,1]-nonane, was prepared by a short enantioselective reduction of an enantiomerically pure β,δ-diketosulfoxide.

New insights into the reduction of β,δ-diketo-sulfoxides

New developments in the reduction of β,δ-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the β-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the δ-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected β,δ-diketo-sulfoxides and showed that judicious protection of the δ-carbonyl group gave all diastereoisomers of β-hydroxy-δ-ketosulfoxides.

Enantioselective synthesis of the unsymmetrical bis(lactone) (-)- (3E,6R,9E,12S,14R)-colletol induced by chiral sulfoxides and an approach to (+)-colletodiol by asymmetric hydroxylation of an α,β-hydroxy lactone

A general synthetic strategy towards the two bis(lactones) (-)colletol (1) and (+)-colletodiol (2) is described. A common intermediate in this synthesis is the 6-membered hydroxy lactone (+)-(3R,5R)-3-hydroxy-5- hexanolide (6), readily prepared by stereos

Chiral sulfoxides in asymmetric synthesis: Enantioselective synthesis of (-)-(5S,7R)-Tarchonanthuslactone

The enantioselective synthesis of (-)-(5S,7R)-Tarchonanthuslactone, a substituted δ-lactone isolated from a compositae, is described. The main feature of this short synthesis is the stereoselective reduction of a β,δ-diketosulfoxide affording in 6 steps t

Chiral sulfoxides in asymmetric synthesis: Enantioselective synthesis of the lactonic moiety of (+)-compactin and (+)-mevinolin. Application to a compactin analogue

The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a β,δ-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of β,δ-diketo sulfoxide without any protective group.