33156-94-4

Upstream product

• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 197773-72-1 (1R,2R)-1-hex-1'-enyl-2-vinyl-cyclopropane 
• 75658-86-5 (1S,5R)-3-oxabicyclo[3.1.0]hexan-2-one 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 19493-09-5 Methylenetriphenylphosphorane 
• 98392-31-5 cis-(1R,2R)-1-formyl-2-<(E)-hex-1-enyl>cyclopropane 

Relevant academic research and scientific papers

Pericyclic reactions in nature: Synthesis and Cope rearrangement of thermolabile bis-alkenylcyclopropanes from female gametes of marine brown algae (Phaeophyceae)

The biosyntheses of the 6-substituted cyclohepta-1,4-dienes dictyotene (1), ectocarpene (2), desmarestene (3), vinylcycloheptadiene (4) and lamoxirene (5) involve a spontaneous Cope rearrangement of thermolabile bis-alkenylcyclopropane precursors like 16,

ENZYMATIC HYDROLYSIS OF CYCLOPROPANES. TOTAL SYNTHESIS OF OPTICALLY PURE DICTYOPTERENES A AND C'.

Enzymatic hydrolysis of cis-1,2-bis(butyryloxymethyl)cyclopropane 3 under optimized conditions gives, in quantitative yield, optically pure cis-(1S,2R)-1-hydroxymethyl-2-butyryloxymethylcyclopropane 1.This compound is a versatile cyclopropane synthon as exemplified by the total synthesis of optically pure seaweed pheromones Dictyopterenes A and C'.

ENANTIOSELECTIVE SYNTHESIS OF DICTYOPTERENE C 6R-(-)-BUTYL-2,5-CYCLOHEPTADIENE THE PHEROMONE OF SEVERAL DICTYOTALES (PHAEOPHYCEAE)

R-(-)-Dictyopterene C (1) is a widespread constituent of many marine brown algae (Phaeophyceae).A highly enantioselective synthesis of 1 and its enantiomer ent-1 via chromatographic separation of the diastereomeric γ-hydroxyphenylethylamide intermediates 3a and 3b is described.