107290-98-2

Upstream product

• 61045-33-8 diethyl (2R,3R)-1,4-dioxaspiro[4.5]decane-2,3-dicarboxylate 
• 108-94-1 cyclohexanone 
• 933-40-4 cycloxexanone dimethyl ketal 
• 60989-82-4 (2S,3S)-(–)-2,3-di(hydroxymethyl)-1,4-dioxaspiro[4.5]decane 
• 100-39-0 benzyl bromide 

Downstream Products

• 86462-53-5 Benzyl-[(S)-2-dimethylcarbamoyl-1-((2S,3S)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-carbamic acid benzyl ester 
• 86462-52-4 (S)-3-Benzylamino-N,N-dimethyl-3-((2S,3S)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propionamide 
• 86462-51-3 Benzyl-[1-((2S,3S)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-amine 
• 107291-01-0 (-)-(2S,3S)-2-benzyloxymethyl-3-<3-hydroxy-2-methyl-1(E)-propenyl>-1,4-dioxaspiro<4,5>decane 
• 107290-99-3 (2R,3S)-3-Benzyloxymethyl-1,4-dioxa-spiro[4.5]decane-2-carbaldehyde 

Relevant academic research and scientific papers

SYNTHETIC STUDIES TOWARDS (-)-QUASSIMARIN: AN INTRAMOLECULAR DIELS-ALDER APPROACH TO THE BCE RING SYSTEM

A novel and a chiral approach to the synthesis of BCE ring system of (-)-quassimarin is described which involves an intramolecular Diels-Alder reaction of the trienic precursor (18) as a key step.The key dihydrofuranone (17) was prepared from L-(+)-diethyl tartrate via 14 step sequence.The quaternary carbon centre in (17) was stereoselectively constructed by magnesium chelation controlled addition of α-lithio-α-methoxyallene to α,β-dialkoxy ketone.Thermolysis of the triene (18) and subsequent hydrolysis provided two tricyclic cycloadducts (19) and (20), both structures were characterized spectroscopically as the corresponding acetates (21) and (22).Particularly, the major adduct (21) was established by the X-ray crystallographic analysis.

STEREOSELECTIVE SYNTHESIS OF L-DAUNOSAMINE

L-Daunosamine was conveniently synthesized from β-amino amide 1 obtained by stereoselective addition of α-lithio N,N-dimethylacetamide to the imine of 2,3-O-cyclohexylidene-4-deoxy-L-threose in the presence of zinc halide.