163513-81-3

Usage

Uses

Used in Pharmaceutical Industry:
Triptoquinide is used as an anti-malarial agent for its ability to inhibit the growth of Plasmodium falciparum, the parasite that causes malaria. Its low cytotoxicity to human cells suggests that it could be a safe and effective treatment option for malaria, pending further research into its mechanism of action and potential applications in the treatment of this disease.

Upstream product

• 74311-48-1 (3bR,9bS)-7-isopropyl-6-methoxy-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[2,1-c]furan-1(3H)-one 
• 74285-86-2 14-hydroxy-19-(4->3)-abeo-abieta-3,8,11,13-tetraen-19,18-olide 

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).