A Concise, Stereocontrolled Total Synthesis of Rippertenol

Snyder, Scott A.; Wespe, Daniel A.; Hof, Jana

doi:10.1021/ja202859f

Cited by 40 publications

(30 citation statements)

References 40 publications

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“…Snyder and co-workersh ave designed at otal synthesis with early stereoselective installation of the quaternary methyl groups. [107] The seven-membered ring is the last to be formed, as Snyder notes that an iEDDA reactionw ould be able to control the diastereoselectivity.S ubsequently,r ing expansion would afford the seven-membered ring of rippertenol. Thus, the iEDDA reaction between 86 and 87 is complete in 10 min, and the adduct is obtained in 68 %y ield with ad iastereoselectivity of 2.6:1 ( Figure 28).…”

Section: Rippertenolmentioning

confidence: 99%

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

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Zeng

et al. 2017

Chemistry An Asian Journal

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Inverse-electron-demand Diels-Alder (iEDDA) reactions are an intriguing class of cycloaddition reactions that have attracted increasing attention for their application in bioorthogonal chemistry, the total synthesis of natural products, and materials science. In many cases, the application of the iEDDA reaction has been demonstrated as an innovative approach to achieve target structures. The theoretical aspects of this class of reactions are of particular interest for scientists as a means to understand the various factors, such as steric strain and electron density of the attached groups, that govern the reaction and thus to elucidate the reaction mechanism. This review aims to summarize both theoretical investigations and application-driven research work on the iEDDA reaction. First, the historical aspects and the theoretical basis of the reaction, especially recent advances in time-dependent density functional theory (TD-DFT) calculations, as well as catalysis strategies will be highlighted and discussed. Second, the applications of this novel reaction in the context of materials science, bioorthogonal chemistry, and total synthesis of natural products will be elaborated with selected recent examples. The challenges and opportunities of the iEDDA reaction will be highlighted to give more insight into its potential applications in many other research areas.

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Section: Rippertenolmentioning

confidence: 99%

Inverse‐Electron‐Demand Diels–Alder Reactions: Principles and Applications

Png

Zeng

et al. 2017

Chemistry An Asian Journal

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“…In addition to its conformational flexibility, 157 is devoid of common functional groups, and a lack of such synthetic handles can complicate terpene syntheses. 200 A non-stereoselective synthesis of 157 was first reported in 1980, 201 followed by a stereoselective, racemic synthesis by Kodama in 1982. 202 To date, two asymmetric routes to (+)-cubitene have been disclosed, both of which utilized chiral pool materials: Kodano’s 1996 synthesis from D-mannitol, 203 and Lindel’s 2012 synthesis from carvone.…”

Section: Syntheses From the 21st Centurymentioning

confidence: 99%

Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products

et al. 2017

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The pool of abundant chiral terpene building blocks (i.e. “chiral pool terpenes”) has long served as a starting point for the chemical synthesis of complex natural products, including many terpenes themselves. As inexpensive and versatile starting materials, such compounds continue to influence modern synthetic chemistry. This review highlights 21st century terpene total syntheses which themselves use small, terpene-derived materials as building blocks. An outlook to the future of research in this area is highlighted as well.

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“…Die Synthesen dieser Naturstoffe sind ebenfalls weitgehend unerforscht. Kempen‐2 ( 2 ) und Rippertan 3 wurden von Dauben et al. bzw.…”

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