Synthesis of 4-
            <i>Desmethyl</i>
            -Rippertenol and 7-
            <i>Epi</i>
            -Rippertenol via Photoinduced Cyclization of Dienones

Zhang, Zi-Chun; Zhao, Dandan; Zhong-chao, Zhang; Tan, Xin-Yu; Gong, Jianxian; Fu, Junkai; Yang, Zhen

doi:10.31635/ccschem.020.202000398

Cited by 4 publications

(3 citation statements)

References 66 publications

(71 reference statements)

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“…Fu, J.-K. Yang, Z. CCS Chem.2020220742083 . This work illustrates concise syntheses of 4-desmethyl-rippertenol and 7-epi-rippertenol based on an intramolecular Pauson–Khand reaction and a novel photoinduced intramolecular cyclization of α-cyclopropyl dienone as key steps. Total Synthesis of (+)-Haperforin GZhangW.ZhangZ.-Y.TangJ.-C.CheJ.-T.ZhangH.-Y.ChenJ.-H.YangZ. Zhang, W. Zhang, Z.-Y.…”

Section: Key Referencesmentioning

confidence: 85%

“…41 In 2020, we reported our effort to develop a concise approach to the asymmetric total synthesis of 4-desmethyl-rippertenol (8) with PK reaction and UV-light-induced cyclization reaction as the key steps. 3 Figure 7 shows our retrosynthetic analysis. We envisioned that the cyclohepta-1,3-diene motif in 8 could be constructed via a UV-light-induced cyclization of α-cyclopropyl-substituted dienone D-1.…”

Section: ■ Total Synthesis Of Crinipellin Amentioning

confidence: 99%

“…In 2011, the Snyder group presented the first total synthesis of rippertenol by using an inverse electron-demand Diels–Alder reaction and late-stage ring expansion to forge the fused cycloheptanoid structure . In 2020, we reported our effort to develop a concise approach to the asymmetric total synthesis of 4-desmethyl-rippertenol ( 8 ) with PK reaction and UV-light-induced cyclization reaction as the key steps …”

Section: Total Synthesis Of (+)-4-desmethyl-rippertenolmentioning

confidence: 99%

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Navigating the Pauson–Khand Reaction in Total Syntheses of Complex Natural Products

Yang

2021

Acc. Chem. Res.

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Conspectus “Total synthesis endeavors provide wonderful opportunities to discover and invent new synthetic reactions as a means to advance organic synthesis in general. Such discoveries and inventions can occur when the practitioner faces intransigent problems that cannot be solved by known methods and/or when method improvements are desired in terms of elegance, efficiency, cost-effectiveness, practicality, or environmental friendliness” (K. C. Nicolaou et al. from their review in CCS Chem.20191337). To date tens of thousands of bioactive compounds have been isolated from plants, microbes, marine invertebrates, and other sources. These chemical structures have been studied by chemists who scanned the breadth of natural diversity toward drug discovery efforts. Drug-likeness of natural products often possesses common features including molecular complexity, protein-binding ability, structural rigidity, and three-dimensionality. Considering certain biologically important natural products are scarce from natural supply, total synthesis may provide an alternative solution to generating these compounds and their derivatives for the purpose of probing their biological functions. Natural products bearing quaternary carbon stereocenters represent a group of biologically important natural entities that are lead compounds in the development of pharmacological agents and biological probes. However, the stereocontrolled introduction of quaternary carbons, with vicinal patterns that substantially expand the complexity of molecular architectures and chemical space in particular, presents distinct challenges because of the high steric repulsion between substituents. Though remarkable advance has been seen for quaternary carbon stereocenter generation, the process remains a daunting challenge given that the formation of highly congested stereocenters increases the difficulty in achieving orbital overlap. In the past two decades, our group has initiated a program to develop synthetic strategies and methods with the aim of advancing the frontiers of the total syntheses of biologically important complex natural products bearing all-carbon quaternary stereogenic centers. Typical endeavors have involved the use of a Pauson–Khand (PK) reaction as a key step in constructing core structures with all-carbon quaternary stereogenic center(s), with the aid of well-orchestrated thiourea–Co- and thiourea–Pd-catalyzed PK reactions. These methodological advances have enabled us to achieve total syntheses of a series of topologically complex natural products with diverse structural features. These methods will enable the assembly of molecules with improved biological functions and provide tool compounds for elucidation of mechanism of action or identification of potential cellular targets.

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Section: Key Referencesmentioning

confidence: 85%

Section: ■ Total Synthesis Of Crinipellin Amentioning

confidence: 99%

Section: Total Synthesis Of (+)-4-desmethyl-rippertenolmentioning

confidence: 99%

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Navigating the Pauson–Khand Reaction in Total Syntheses of Complex Natural Products

Yang

2021

Acc. Chem. Res.

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Rhodium-Catalyzed [7 + 1] Cycloaddition of Exocyclic 1,3-Dienylcyclopropanes and Carbon Monoxide

Huang,

Wang,

Jin

et al. 2023

Org. Lett.

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Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

et al. 2020

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Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated.

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Synthesis of 4- Desmethyl -Rippertenol and 7- Epi -Rippertenol via Photoinduced Cyclization of Dienones

Cited by 4 publications

References 66 publications

Navigating the Pauson–Khand Reaction in Total Syntheses of Complex Natural Products

Navigating the Pauson–Khand Reaction in Total Syntheses of Complex Natural Products

Rhodium-Catalyzed [7 + 1] Cycloaddition of Exocyclic 1,3-Dienylcyclopropanes and Carbon Monoxide

Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

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