264610-07-3

Upstream product

• 263157-65-9 1-((E)-5-Bromo-4-methyl-pent-3-enyl)-3-isopropyl-2-methoxy-benzene 
• 264609-98-5 (-)-8-phenylmenthyl 2-chloroacetoacetate 
• 90358-31-9 (+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate 
• 74931-59-2 1-isopropyl-2-methoxymethyloxybenzene 
• 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 
• 88-69-7 2-(1-methylethyl)phenol 

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).