cas 74285-86-2, TRIPTOPHENOLIDE | Articles data ｜lookchem

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74285-86-2

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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).
Yang, Dan,Ye, Xiang-Yang,Xu, Ming
p. 2208 - 2217
(2007/10/03)

Lanthanide triflates catalyze Mn(III)-Based oxidative radical cyclization reactions. Enantioselective synthesis of (-)-triptolide, (-)- Triptonide, and (+)-Triptophenolide
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Yang, Dan,Ye, Xiang-Yang,Gu, Shen,Xu, Ming
p. 5579 - 5580
(2007/10/03)

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163513-81-3
11,14-dioxo-19-(4->3)-abeo-abieta-3,8,12-trien-19,18-olide

Chemical Properties

Appearance/Colour :white powder
Melting Point: 232-233oC
Boiling Point: 490 °C at 760 mmHg
Flash Point:202.4 °C
Density: 1.21 g/cm³
Vapor Pressure: 3.16E-10mmHg at 25°C
Refractive Index: 1.603
PKA: 10.63±0.40(Predicted)
PSA: 46.53000
LogP: 3.98290

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