74311-48-1

Usage

Uses

Triptophenolide methyl ether is a useful research chemical.

InChI:InChI=1/C21H26O3/c1-12(2)13-5-7-17-15(19(13)23-4)6-8-18-16-11-24-20(22)14(16)9-10-21(17,18)3/h5,7,12,18H,6,8-11H2,1-4H3/t18-,21+/m0/s1

Upstream product

• 201230-82-2 carbon monoxide 
• 238746-44-6 Trifluoro-methanesulfonic acid (4aS,10aR)-1-hydroxymethyl-7-isopropyl-8-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydro-phenanthren-2-yl ester 
• 6099-03-2 3-(2'-methoxyphenyl)propenoic acid 
• 1238621-34-5 (E)-ethyl 7-(2-methoxyphenyl)-4-methylhept-4-enoate 
• 288321-56-2 1-Methyl-1-(1'-methylethenyl)silacyclobutane 
• 1209485-40-4 (3bR,9bS)-6-methoxy-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[1,2-c]furan-1(3H)-one 
• 238746-42-4 (1S,4aS,10aS)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 238746-43-5 (4aS,10aR)-7-Isopropyl-8-methoxy-4a-methyl-2-trifluoromethanesulfonyloxy-3,4,4a,9,10,10a-hexahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 163513-81-3 11,14-dioxo-19-(4->3)-abeo-abieta-3,8,12-trien-19,18-olide 
• 225786-93-6 (3bR,9bS)-7-Isopropyl-6-methoxy-9b-methyl-3,3b,4,9b,10,11-hexahydro-phenanthro[1,2-c]furan-1,5-dione 
• 74285-86-2 14-hydroxy-19-(4->3)-abeo-abieta-3,8,11,13-tetraen-19,18-olide 
• 38647-11-9 l-triptonide 

Relevant academic research and scientific papers

Divergent total synthesis of triptolide, triptonide, tripdiolide, 16-hydroxytriptolide, and their analogues

A divergent route was developed for the formal total synthesis of triptolide, triptonide, and tripdiolide, as well as a total synthesis of 16-hydroxytriptolide and their analogues in an enantioselective form. Common advanced intermediate 5 was concisely assembled by employing an indium(III)-catalyzed cationic polycyclization reaction and a palladium-catalyzed carbonylation-lactone formation reaction as key steps. This advanced intermediate was readily converted to the above natural products by using palladium-catalyzed cross-coupling or the Claisen rearrangement reaction as key steps. Additionally, preliminary structure-cytotoxic activity relationship studies of C13 suggested that it might be a new modification site that could still retain the cytotoxicity.

Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide

An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (-)-triptolide 1.The route is of characteristic of low cost, high yield and easy operation.In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.

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).