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Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent. / Mironov, M. E.; Shults, E. E.

In: Russian Chemical Bulletin, Vol. 72, No. 10, 10.2023, p. 2453-2465.

Research output: Contribution to journal › Article › peer-review

Harvard

Mironov, ME & Shults, EE 2023, 'Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent', Russian Chemical Bulletin, vol. 72, no. 10, pp. 2453-2465. https://doi.org/10.1007/s11172-023-4047-z

APA

Mironov, M. E., & Shults, E. E. (2023). Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent. Russian Chemical Bulletin, 72(10), 2453-2465. https://doi.org/10.1007/s11172-023-4047-z

Vancouver

Mironov ME, Shults EE. Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent. Russian Chemical Bulletin. 2023 Oct;72(10):2453-2465. doi: 10.1007/s11172-023-4047-z

Author

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. In: Russian Chemical Bulletin. 2023 ; Vol. 72, No. 10. pp. 2453-2465.

BibTeX

@article{c7c0555625c5484faabb32b415f2bf6e,
title = "Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent",
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{\textquoteright}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.",
keywords = "diterpenoids, enones, furans, labdanoids, multicomponent reactions, organocatalysis, silyloxybutadienes, the Diels—Alder reaction, the Suzuki reaction",
author = "Mironov, {M. E.} and Shults, {E. E.}",
note = "This work was financially supported by the Russian Science Foundation (Project No. 23-73-00077). Публикация для корректировки.",
year = "2023",
month = oct,
doi = "10.1007/s11172-023-4047-z",
language = "English",
volume = "72",
pages = "2453--2465",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "10",

}

RIS

TY - JOUR

T1 - Synthesis and transformations of 2,4-dioxa- and 2,4-diazaspiro[5.5]undecanones equipped with a diterpenoid substituent

AU - Mironov, M. E.

AU - Shults, E. E.

N1 - This work was financially supported by the Russian Science Foundation (Project No. 23-73-00077). Публикация для корректировки.

PY - 2023/10

Y1 - 2023/10

N2 - 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.

AB - 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.

KW - diterpenoids

KW - enones

KW - furans

KW - labdanoids

KW - multicomponent reactions

KW - organocatalysis

KW - silyloxybutadienes

KW - the Diels—Alder reaction

KW - the Suzuki reaction

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85176087146&origin=inward&txGid=5c7e36e66add4d7cd96080d941dca5a5

UR - https://www.mendeley.com/catalogue/6ef08ed5-9db3-3625-915c-1dccdee2f444/

U2 - 10.1007/s11172-023-4047-z

DO - 10.1007/s11172-023-4047-z

M3 - Article

VL - 72

SP - 2453

EP - 2465

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 10

ER -

ID: 59546954