191530-46-8

Upstream product

• 191278-15-6 (1S,8R,9R,10R)-8-phenyl-1-decalyl (S)-[(1-phenylethyl)carbamoyl] phthalate 
• 104197-81-1 (1S*,8R*,9R*,10R*)-8-phenyl-1-decalol 
• 191278-23-6 (1S,8R,9R,10R)-8-phenyl-1-decalol 

Downstream Products

• 191278-16-7 (8R,9R,10R)-8-phenyl-1-methylenedecalin 
• 191278-10-1 (1S,8R,9R,10R)-1-methyl-8-phenyl-1-decalyl 2-(hydroxyimino)-3-(2-hydroxy-3,5-dibromo-4-methoxyphenyl)propionate 
• 191278-21-4 (1S,8R,9R,10R)-1-methyl-8-phenyl-1-decalyl 2-[(benzyloxy)imino]-3-[2-(benzyloxy)-3,5-dibromo-4-methoxyphenyl]propionate 
• 191278-12-3 (1S,8R,9R,10R)-1-methyl-8-phenyl-1-decalol 

Relevant academic research and scientific papers

Asymmetric Oxidative Cyclization of o-Phenolic Oxime-Esters: First Synthesis of Enantiomerically Enriched Spiroisoxazoline Methyl Esters

A new method for the synthesis of enantiomerically enriched cyclohexadienone spiroisoxazoline (-)-2a has been described. Asymmetric intramolecular oxidative cyclization of the o-phenolic oximeester 1c using a novel optically active tertiary alcohol (-)-3 as a chiral auxiliary proceeded smoothly to afford cyclohexadienone spiroisoxazoline 2c in 83% yield. Opitcally active tertiary alcohol (-)-3 was synthesizied from racemic (1S*,8R*,9R*,10R*)-8-phenyl-1-decalol (4) by optical resolution. Removal of the chiral auxiliary in 2c with CF3COOH followed by methylation gave methyl ester (-)-2a in 74% ee (71% chemical yield) having S-configuration. The absolute configuration of 2a was determined by the synthesis of the marine natural product (+)-aerothionin.