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Effective Synthesis of a Novel Tetrahydrofuran Containing Triterpenoid: 5′(Z)-Benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate

1
Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075 Ufa, Russia
2
Bashkir State University, 32 Zaki Validi Str., 450076 Ufa, Russia
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Author to whom correspondence should be addressed.
Molbank 2019, 2019(1), M1042; https://doi.org/10.3390/M1042
Received: 4 December 2018 / Revised: 21 December 2018 / Accepted: 27 December 2018 / Published: 28 December 2018
(This article belongs to the Section Organic Synthesis)
The title compound 5′(Z)-benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate was synthesized with high chemo-, regio-, and stereoselectivity by 5-exo-dig cycloisomerization of methyl 2α-phenylpropynyl-3-oxolup-20(29)-en-28-oate with use of KN(SiMe3)2-DME. The novel betulinic acid derivative was fully characterized by conventional analytical methods and all proton and carbon signals have been completely assigned by 2D-NMR experiments. View Full-Text
Keywords: betulinic acid; alkynes; tetrahydrofuranes; 5-exo-dig heterocyclization betulinic acid; alkynes; tetrahydrofuranes; 5-exo-dig heterocyclization
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MDPI and ACS Style

Gubaidullin, R.; Nedopekina, D.; Evstifeeva, R.; Prochukhan, Y. Effective Synthesis of a Novel Tetrahydrofuran Containing Triterpenoid: 5′(Z)-Benzylidene-tetrahydrofurano[3,2-b]lup-20(29)-en-28-oate. Molbank 2019, 2019, M1042.

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