Abstract: The Diels—Alder reaction of 16-(3-trimethylsilyloxybutadienyl)furanolabdanoids with 5-methylene(arylidene)-3,3-dimethyl-2,4-dioxane-1,5-diones or 5-methylene(arylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones in the presence of L-proline proceeded regioselectively and led to 7-furanoterpenyl-substituted 3,3-dimethyl-2,4-dioxaspiro[5.5]-undecane-1,5,9-triones or 2,4-dimethyl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraones, respectively. The conditions for the one-pot synthesis of terpenyl-substituted dioxaspiro-[5.5]undecane-1,5,9-triones by the L-proline catalyzed three-component Knoevenagel—Diels—Alder reaction of diterpenoid enone, aldehyde, and the Meldrum’s acid were proposed. A diterpenoid analog of anticancer agents with an 11-(biphenyl-4-yl)-2,4-di-oxaspiro[5.5]undecanone substituent was synthesized by the Suzuki reaction of the obtained bromophenyl-substituted spirocyclic ketone with 3,4,5-(trimethoxyphenyl)boronic acid.

Cite: Mironov M.E. , Shults E.E.
Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent
Russian Chemical Bulletin. 2023. V.72. N10. P.2453-2465. DOI: 10.1007/s11172-023-4047-z WOS Scopus РИНЦ

ArticleLinkType.TRANSLATED_TO_ORIGINAL: Миронов М.Е. , Шульц Э.Э.
Синтез и превращения 2,4-диокса- и 2,4-диазаспиро[5.5]ундеканонов, содержащих дитерпеноидный заместитель
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2023. Т.72. №10. С.2453-2465. РИНЦ

Dates:

Published online:

Nov 11, 2023

Identifiers:

Web of science	WOS:001103056900022
Scopus	2-s2.0-85176087146
Elibrary	64105985
OpenAlex	W4388594288

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