269719-13-3

Upstream product

• 38011-83-5 trans-1-(4,8-dimethylnona-3,7-dien-1-yl)-4-methoxybenzene 
• 52567-43-8 (S)-Methyl-α-cyclogeraniumsaeure 
• 14505-74-9 (S)-2,6,6-trimethylcyclohex-2-enecarbaldehyde 
• 52646-93-2 [(S)-2,6,6-trimethylcyclohex-2-enyl]methanol 
• 24190-30-5 (S)-α-cyclogeraniumsaeure 
• 4698-08-2 (E)-geranic acid 
• 269719-12-2 3-(4-methoxystyryl)-2,4,4-trimethyl-1-cyclohexene 

Relevant academic research and scientific papers

Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs. A new entry to (-)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (-)-tetracyclic polyprenoid of sedimentary origin

An enantio- and diastereoselective stepwise cyclization of polyprenoids induced by Lewis acid-assisted chiral Bronsted acids (chiral LBAs) and achiral LBAs is described. In particular, the absolute stereocontrol in the initial cyclization of polyprenoids to form an A-ring induced by chiral LBAs and the importance of the nucleophilicity of the internal terminator in polyprenoids for the relative stereocontrol in subsequent cyclization are demonstrated. (-)-Ambrox was synthesized via the enantioselective cyclization of (E,E)-homofarnesyl triethyrsily ether with triethylsilyl ether with tin(IV) chloride-coordinated (R)-2-(o-fluorobenzyloxy)-2′-hydroxy-1,1′-binaphthyl ((R)-BINOL-o-FBn) and subsequent diastereoselective cyclization with CF3CO2H·SnCl4 as key steps. Protection of (E,E)-homofarnesol by a triethylsilyl group increased the enantioselectivity of chiral LBA-induced cyclization and both the chemical yield and diastereoselectivity in the subsequent cyclization. The enantioselective cyclization of homo(polyprenyl)arenes possessing an aryl group was also induced by (R)-BINOL-o-FBn·SnCl4. Several optically active podocarpa-8,11,13-triene diterpenoids and (-)-tetracyclic polyprenoid of sedimentary origin were synthesized (75-80% ee) by the enantioselective cyclization of homo(polyprenyl)benzene derivatives induced by (R)-BINOL-o-FBn·SnCl4 and subsequent diastereoselective cyclization induced by BF3-Et2O/EtNO2 or CF3CO2H·SnCl4.

Stereoselective synthesis of (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether

A facile stereoselective synthetic procedure to (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether has been developed with high stereoselectivity and overall yield.

Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether

A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-α-cyclocitral. Copyright (C) 2000 Elsevier Science Ltd.