One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid

Galimova, Zarema; Smirnova, Irina; Lobov, Alexander; Polovyanenko, Dmitriy; Rybalova, Tatyana; Kazakova, Oxana

doi:10.3390/ijms25158356

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One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid

by

Zarema Galimova

¹,

Irina Smirnova

^1,*

,

Alexander Lobov

¹

,

Dmitriy Polovyanenko

²,

Tatyana Rybalova

²

and

Oxana Kazakova

¹

Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71, pr. Oktyabrya, 450054 Ufa, Russia

²

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, 630090 Novosibirsk, Russia

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2024, 25(15), 8356; https://doi.org/10.3390/ijms25158356 (registering DOI)

Submission received: 30 June 2024 / Revised: 18 July 2024 / Accepted: 26 July 2024 / Published: 30 July 2024

(This article belongs to the Special Issue Development of Biologically Active Compounds – Design, Synthesis and Application)

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Abstract

Hollongdione is the first recorded example of the occurrence of a dammarane hexanor-triterpene in nature possessing antiviral and cytotoxic activity. Its simple one-stage transformation into compounds with terminal alkyne and vinyl chloride fragments via the interaction with phosphorus halides is reported. The copper(I)-catalyzed Mannich reaction of 3-oxo-22,23,24,25,26,27-hexanor-dammar-20(21)-in 3 led to a series of aminomethylated products, while 17-carboxylic acid was obtained by ozone oxidation of 3-oxo-22,23,24,25,26,27-hexanor-dammar-20-chlorо-20(21)-en 4; the following direct amidation of the latter has been developed. The structures of all new molecules were established by spectroscopic studies that included 2D NMR correlation methods; the molecular structures of compounds 2–5 were determined by X-ray analysis.

Keywords: dammarane triterpenoids; hollongdione; alkyne; vinyl chloride; Mannich base; hollongdionoic acid

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MDPI and ACS Style

Galimova, Z.; Smirnova, I.; Lobov, A.; Polovyanenko, D.; Rybalova, T.; Kazakova, O. One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid. Int. J. Mol. Sci. 2024, 25, 8356. https://doi.org/10.3390/ijms25158356

AMA Style

Galimova Z, Smirnova I, Lobov A, Polovyanenko D, Rybalova T, Kazakova O. One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid. International Journal of Molecular Sciences. 2024; 25(15):8356. https://doi.org/10.3390/ijms25158356

Chicago/Turabian Style

Galimova, Zarema, Irina Smirnova, Alexander Lobov, Dmitriy Polovyanenko, Tatyana Rybalova, and Oxana Kazakova. 2024. "One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid" International Journal of Molecular Sciences 25, no. 15: 8356. https://doi.org/10.3390/ijms25158356

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One-Stage Pathway from Hollongdione to C17-Alkyne and Vinyl Chloride Following Mannich Bases and Carboxylic Acid

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