Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent Full article
| Journal |
Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171 |
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| Output data | Year: 2023, Volume: 72, Number: 10, Pages: 2453-2465 Pages count : 13 DOI: 10.1007/s11172-023-4047-z | ||||
| Tags | diterpenoids, labdanoids, furans, silyloxybutаdienes, enones, organocatalysis, the Diels—Alder reaction, multicomponent reactions, the Suzuki reaction. | ||||
| Authors |
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Funding (1)
| 1 | Российский Научный Фонд | 23-73-00077 |
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 OpenAlex
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 OpenAlex
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
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 |