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A Modular Approach for the Synthesis of Natural and Artificial Terpenoids.
Wang, Weiyi; Huang, Dongyu; Yu, Yibo; Qian, Hui; Ma, Shengming.
Afiliación
  • Wang W; Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
  • Huang D; Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
  • Yu Y; Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
  • Qian H; Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
  • Ma S; Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433, P. R. China.
Angew Chem Int Ed Engl ; 62(37): e202307626, 2023 09 11.
Article en En | MEDLINE | ID: mdl-37439109
Many terpenoids with isoprene unit(s) demonstrating critical biological activities have been isolated and characterized. In this study, we have developed a robust chem-stamp strategy for the construction of the key isoprene unit, which consists of two steps: one-carbon extension of aldehydes to the alkenyl boronates by the boron-Wittig reaction and the rhodium-catalyzed reaction of alkenyl boronates with 2,3-allenols to yield enals. This chem-stamp could readily be applied repeatedly and separately, enabling the modular concise synthesis of many natural and pharmaceutically active terpenoids, including retinal, ß-carotene, vitamin A, tretinoin, fenretinide, acitretin, ALRT1550, nigerapyrone C, peretinoin, and lycopene. Owing to the diversified availability of the starting materials, aldehydes and 2,3-allenols, creation of new non-natural terpenoids has been realized from four dimensions: the number of isoprene units, the side chain, and the two terminal groups.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Terpenos / Hemiterpenos Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article Pais de publicación: Alemania
Texto completo
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Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Terpenos / Hemiterpenos Idioma: En Revista: Angew Chem Int Ed Engl Año: 2023 Tipo del documento: Article Pais de publicación: Alemania