214077-11-9

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 263157-65-9 1-((E)-5-Bromo-4-methyl-pent-3-enyl)-3-isopropyl-2-methoxy-benzene 
• 263157-60-4 2-isopropyl-6-(4-methyl-pent-3-enyl)-phenol 
• 263157-58-0 1-isopropyl-2-methoxymethoxy-3-methyl-benzene 
• 263157-59-1 1-Isopropyl-2-methoxymethoxy-3-(4-methyl-pent-3-enyl)-benzene 
• 214077-10-8 (E)-5-(3-Isopropyl-2-methoxy-phenyl)-2-methyl-pent-2-en-1-ol 
• 263157-61-5 1-Isopropyl-2-methoxy-3-(4-methyl-pent-3-enyl)-benzene 
• 74931-59-2 1-isopropyl-2-methoxymethyloxybenzene 
• 88-69-7 2-(1-methylethyl)phenol 

Downstream Products

• 238746-41-3 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 238746-38-8 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 322640-56-2 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 73414-41-2 (+/-)-triptophenolide methyl ether 
• 238746-40-2 (1S,4aS,10aS)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 238746-39-9 (1R,4aR,10aR)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 322640-62-0 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-2-[1-(3,5-diisopropoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 
• 322640-51-7 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-2-[1-(3,5-diisopropoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 
• 322640-57-3 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-2-(1-biphenyl-4-yl-1-methyl-ethyl)-5-methyl-cyclohexyl ester 
• 322640-60-8 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-2-[1-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 
• 322640-61-9 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-2-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 
• 322640-50-6 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1R,2S,5R)-2-[1-(3,5-dimethoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 
• 322640-53-9 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-5-methyl-2-[1-methyl-1-(4-nitro-phenyl)-ethyl]-cyclohexyl ester 
• 322640-58-4 (E)-9-(3-Isopropyl-2-methoxy-phenyl)-6-methyl-3-oxo-non-6-enoic acid (1S,2S,5R)-2-[1-(4-methoxy-phenyl)-1-methyl-ethyl]-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of (-)-Triptolide, (-)-Triptonide, (+)-Triptophenolide, and (+)-Triptoquinonide

The first enantioselective total synthesis of (-)-triptolide (1), (-)-triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc)9, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)-Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).