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Asymmetric total synthesis of penicilfuranone A through an NHC-catalyzed umpolung strategy

Year: 2025

Type: article

Abstract: The first asymmetric total synthesis of penicifuranone A was accomplished in eight steps through an NHC-catalyzed umpolung strategy. Key features of the synthesis include an Al-Salen catalyzed asymmetric cyanosilylation to install the tertiary alcohol of gregatin A, and an NHC catalyzed Stetter-Aldol cascade reaction. The umpolung strategy of the benzyl aldehyde fragment facilitated a convergent formal [4 + 2] annulation with gregatin A, ultimately leading to the formation of penicifuranone A.

Source: Chemical Science

DOI: 10.1039/d5sc01508a

Authors: Yiming Ding, Xianwen Long, Jingwei Zhang, Chunlei Qu, Peng Wang, Xiaodong Yang, Pema-Tenzin Puno, Jun Deng

Institutions: Yunnan University, Nankai University, State Key Laboratory of Elemental Organic Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, China Postdoctoral Science Foundation, Nankai University, Fundamental Research Funds for the Central Universities

Awards: G1089046314, G157657956, G195801674, G3381956068, G372628752, G4855278923, G5374741945, G5709232556, G8264846888, G8385610713, G8476429284, G892794816

OpenAlex ID: W4409239763

FWCI: 2.615

Cites: 75

Cited by: 9

Related to: 10