35936-15-3

Upstream product

• 566928-21-0 (1S,2R)-1-formyl-2-hexylcyclopropane 
• 809279-01-4 (1S,2R)-1-butyroyloxymethyl-2-(hex-1'-en-1'-yl)cyclopropane 
• 2984-50-1 (2S)-2-hexyloxirane 
• 395676-56-9 (1R,2R)-2-(n-hexyl)-cyclopropane carboxylic acid ethyl ester 
• 566928-18-5 (1S,2R)-1-butyroyloxymethyl-2-formylcyclopropane 
• 566928-20-9 (1S,2R)-2-hexyl-1-hydroxymethylcyclopropane 
• 252009-93-1 butyric acid (1S,2R)-2-hydroxymethylcyclopropylmethyl ester 
• 151766-40-4 (1S,2S)-2-(hex-1'-en-1'-yl)-1-hydroxymethylcyclopropane 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 441313-03-7 (R,R)-2-hexylcyclopropanecarboxaldehyde 
• 809279-04-7 2-((1S,2R)-2-hexylcyclopropyl)acetonitrile 
• 87626-07-1 4-(1-Methylene-heptyl)-oxetan-2-one 

Relevant academic research and scientific papers

The absolute stereochemistry of cascarillic acid

((1S,2R)-2-Hexylcycloprop-1-yl)acetic acid has been synthesised from cis-1,2-dihydroxymethylcyclopropane and shown to be identical to cascarillic acid obtained from cascarilla essential oil.

CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF

The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.

Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: Application to the synthesis of cascarillic acid, grenadamide and l-(-)-CCG-II

An efficient high yielding improved method for the enantio- and diastereoselective cyclopropanation of chiral epoxides using triethylphosphonoacetate and base (Wadsworth-Emmons cyclopropanation) is reported. The utility of this protocol is illustrated by concise and practical synthesis of cascarillic acid, grenadamide and L-(-)-CCG-II, a cyclopropane containing natural products.

A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes

A novel way of combining chiral auxiliaries and substrate directable reactions is described that employs a three-step sequence of aldol/cyclopropanation/retro-aldol reactions for the asymmetric synthesis of enantiopure cyclopropane-carboxaldehydes. In the first step, reaction of the boron enolate of (S)-N-propionyl-5,5-dimethyl-oxazolidin-2-one with a series of α,β-unsaturated aldehydes affords their corresponding syn-aldol products in high de. In the second step, directed cyclopropanation of the alkene functionalities of these syn-aldols occurs under the stereodirecting effect of their 'temporary'β-hydroxyl stereocentres to give a series of cyclopropyl-aldols in high de. Finally, retro-aldol cleavage of the lithium alkoxide of these cyclopropyl-aldols results in destruction of their temporary β-hydroxy stereocentres to afford the parent chiral auxiliary and chiral cyclopropane-carboxaldehydes in >95% ee. The potential of this methodology has been demonstrated for the asymmetric synthesis of the cyclopropane containing natural product cascarillic acid in good yield.

An efficient asymmetric synthesis of cascarillic acid

An efficient six-step asymmetric synthesis of the cyclopropane containing natural product cascarillic acid in 41% overall yield is described. The key synthetic steps involve the use of a temporary stereogenic hydroxyl group to control the facial selectivi

TRANSFORMATION OF β-ALKENYL-β-PROPIOLACTONES INTO CYCLOPROPYLACETIC ACIDS UTILIZING HYDROBORATION

The reaction of β-alkenyl-β-propiolactones with 9-borabicyclononane and subsequent treatment with sodium methoxide gave cyclopropylacetic acids in good yields.