Abstract: The N-(2,3-butadienyl)carboxamide of isopimaric acid, that is, compound 3, was prepared through a two-step synthetic procedure starting from the natural diterpene isopimaric acid. The Pd-catalyzed cross-coupling and subsequent cyclization of terpenoid allene 3 with several aryl iodides and aryl bromides gave access to optically active diterpenoid-oxazoline derivatives in good to excellent yields. The functional group tolerance in the aryl iodides was demonstrated by several examples, including substrates with additional N-tert-butoxycarbonyl-protected amino, hydroxy, and carboxy substituents in the ortho position. The cross-coupling-cyclization reaction of those compounds with allene 3 proceeded selectively with the formation of cyclization products on the substituent in the aromatic ring. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid and several heterocycles.

Cite: Gromova M.A. , Kharitonov Y.V. , Bagryanskaya I.Y. , Shults E.E.
Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids
ChemistryOpen. 2018. V.7. N11. P.890-901. DOI: 10.1002/open.201800205 WOS Scopus РИНЦ

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Dates:

Published print:	Nov 1, 2018
Published online:	Nov 14, 2018

Identifiers:

Web of science	WOS:000451837300007
Scopus	2-s2.0-85057541553
Elibrary	38619518
OpenAlex	W2901977736

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