99341-58-9

Upstream product

• 4605-59-8 trans-4-Hydroxymethyl-2-carene 
• 498-15-7 (+)-Δ³-carene 
• 131509-86-9 (-)-4-methylene-cis-carane 
• 99341-57-8 (-)-cis-carane-trans-4-carboxylic acid 
• 4176-04-9 (1R,4S,6S)-4,7,7-Trimethyl-bicyclo[4.1.0]heptan-3-one 
• 99301-73-2 (+)-trans-4-methoxycarbonyl-cis-carane 
• 59689-64-4 5-Mercapto-3-isopropyl-1,2,4-triazol 

Downstream Products

• 68804-32-0 (-)(1R,3R,4Ξ)-4,7,7-trimethyl-norcarane-3-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of trans-Caran-4-carboxylic Acids

The synthesis of the optically active trans-caran-4-carboxylic acid 4a and 5a is reported.Methylene-cis and trans-caranes (8) and (9) were prepared by Wittig reaction from (-)-cis-caran-4-one (6).The structure of the described compounds are supported by chemical evidence.

Synthesis of Some 4-Cyanocaranes

Four optically active 4-cyanocaranes diastereoisomers have been synthesized starting from (+)-car-3-ene and their structures supported by chemical evidences and X-ray analysis.

STEREOCHEMISTRY OF THE CARANE SYSTEM. PART III. SYNTHESIS AND CHEMICAL TRANSFORMATIONS OF (+)-cis-4-CYANO-cis-CARANE

Sterically homogeneous (+)-cis-4-cyano-cis-carane (4) was obtained by the SN2 reaction of (-)-cis-caran-trans-4-ol tosylate with NaCN in DMF.Alkaline hydrolysis of 4 afforded (-)-cis-carane-trans-4-carboxylic acid (5).The mechanism of hydrolysis, proceeding with inversion of the carbon atom C4, was proposed.Reduction of nitrile 4 and acid 5 with LiAlH4 afforded (-)-cis-4-aminomethyl-cis-carane (9) and (-)-trans-4-hydroxymethyl-cis-carane (7), respectively.The structures of compounds obtained were confirmed by means of spectroscopic methods.