Construction of the A/B/C core of mexicanolides via a tandem double-aldol reaction

[Display omitted] •Cyclohexane-fused bicyclo[3.3.1]nonane is constructed via a cascade process.•LiOH-mediated Micheal reactions delivered the diketoester precursors.•Cascade reaction includes hydrolysis/double aldol reactions/alkene migration. An efficient and concise approach for rapid assembly of...

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Published inTetrahedron letters Vol. 60; no. 35; pp. 150992 - 150994
Main Authors Zhang, Quanzheng, Xu, Dan, Yang, Jiao, He, Ling, Zhang, Min
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.08.2019
Elsevier
Subjects
Aldol reaction
Cascade reaction
Chemistry
Chemistry, Organic
Limonoid
Mexicanolide
Physical Sciences
Science & Technology
Cascade reaction
Mexicanolide
Aldol reaction
Limonoid
MANGROVE
CASCADE REACTIONS
SEEDS
ANDIROBA CARAPA-GUIANENSIS
RING
BIOLOGICAL-ACTIVITY
CHEMISTRY
SWIETENIA-MACROPHYLLA
LIMONOIDS
EFFICIENT
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Summary:[Display omitted] •Cyclohexane-fused bicyclo[3.3.1]nonane is constructed via a cascade process.•LiOH-mediated Micheal reactions delivered the diketoester precursors.•Cascade reaction includes hydrolysis/double aldol reactions/alkene migration. An efficient and concise approach for rapid assembly of the ABC tricyclic carbon skeleton of mexicanolide-type limonoids is described. The acetal/ketal diketoester precursors were prepared from simple starting materials by LiOH-mediated Michael reactions. The ABC tricyclic skeleton bearing multiple stereogenic centers was efficiently constructed by a powerful one-pot cascade reaction, which includes acetal/ketal hydrolysis, double intramolecular aldol condensation, and alkene migration.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.150992