Abstract: Vilsmeier-Haak reaction of phlomisoic acid methyl ester gave a mixture of 15- and 16-formyllabdanoids. In addition, methyl 2-formyldodecahydrophenanthro[1,2-b]furan-6-carboxylate was isolated, and its structure was determined by X-ray analysis. Reductive amination of 16-formyllabdanoid with benzylamine or alpha-amino acid methyl esters led to the formation of labdanoid furfurylamines which reacted with maleic anhydride to produce N-substituted 4-oxo-10-oxa-3-azatricyclo[5.2.1.0(1,5)]dec-8-ene-6-carboxylic acids. Acylation of labdanoid furfurylamines with (E)-but-2-enoyl chloride afforded the corresponding unsaturated amides which were converted into 10-oxa-3-azatricyclo[5.2.1.0(1,5)]dec-8-en-4-ones via intramolecular Diels-Alder reaction. Treatment of the oxa adducts with boron trifluoride-diethyl ether complex gave dihydroisoindol-1-one derivatives containing a diterpene fragment.

Cite: Mironov M.E. , Kharitonov Y.V. , Shul'ts E.E. , Shakirov M.M. , Gatilov Y.V. , Tolstikov G.A.
Synthetic transformations of higher terpenoids: XXIII. Synthesis of diterpenoid-based dihydroisoindolones
Russian Journal of Organic Chemistry. 2010. V.46. N12. P.1869-1882. DOI: 10.1134/S107042801012016X WOS Scopus РИНЦ

Dates:

Published print:	Dec 1, 2010
Published online:	Feb 5, 2011

Identifiers:

Web of science	WOS:000286985900016
Scopus	2-s2.0-79951474339
Elibrary	16698001
OpenAlex	W2162327971

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