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Open AccessCommunication
Molbank 2019, 2019(1), M1042; https://doi.org/10.3390/M1042

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
*
Author to whom correspondence should be addressed.
Received: 4 December 2018 / Revised: 21 December 2018 / Accepted: 27 December 2018 / Published: 28 December 2018
(This article belongs to the Section Organic Synthesis)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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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