79548-61-1Relevant articles and documents
Metal-mediate reactions based formal synthesis of triptonide and triptolide
Xu, Hongtao,Tang, Huanyu,Feng, Huijin,Li, Yuanchao
, p. 7118 - 7120 (2014)
A formal synthesis of triptolide and triptonide has been achieved based on metal-mediate reactions. Specially, Noyori's ruthenium catalyzed enantioselective transfer hydrogenation, indium(III) catalyzed cationic polyene cyclization, palladium catalyzed ca
The triptolide method for the asymmetric synthesis of intermediates
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, (2019/02/02)
The invention relates to a preparation method of an organic compound, and particularly relates to an asymmetric synthesis method of triptolide intermediate namely a compound 4 shown in formula in the specification. The synthesis method comprises the steps of: reacting a compound 5 shown in a formula 2 with a chiral amine reagent; reacting the product with a Nazarov reagent; acidifying to obtain a compound 7; reacting the compound 7 with a sulfonyl esterification reagent to obtain enol sulphonate 8; reducing ester group of the compound 8 to obtain alcohol 9; and finally, obtaining a key intermediate compound 4 for synthesizing triptolide.
POLYCYCLIC EPOXIDES AND COMPOSITIONS THEREOF WITH ANTI-CANCER ACTIVITIES
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, (2016/12/01)
The present technology provides polycyclic epoxides of Formula I, compositions comprising such expoxides and methods of using such epoxides. In particular, these compounds are useful for inhibiting cancer cell proliferation and tumor angiogenesis or treating ovarian, breast, prostate, liver, pancreatic, and colon cancers, as well as leukemia.
New facile enantio- and diastereo-selective syntheses of (-)-triptonide and (-)-triptolide
Zhang, Hongrui,Li, Haifeng,Xue, Jijun,Chen, Rui,Li, Ying,Tang, Yu,Li, Chunxin
, p. 732 - 736 (2014/01/23)
A novel formal asymmetric synthesis of (-)-triptonide and (-)-triptolide, featuring a new alternative access to their known key intermediate 4, has been achieved through two synthetic routes in 9 steps with 13.6% total yield and 10 steps with 18.5% overall yield, respectively. This synthesis is scalable and hence has high potential for application to further synthetic elaboration and biologic investigation on such natural products.
Efficient syntheis of the key intermediate triptophenolide methyl ether for the synthesis of(-)-triptolide
Zhou, Bing,Li, Xiaomei,Feng, Huijin,Li, Yuanchao
experimental part, p. 5396 - 5401 (2010/08/19)
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
Yang, Dan,Ye, Xiang-Yang,Xu, Ming
, p. 2208 - 2217 (2007/10/03)
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).
