Oxetanes as versatile building blocks in the total synthesis of natural products: An overview

Mahal, Ahmed

doi:10.5155/eurjchem.6.3.357-366.1267

Cited by 26 publications

(6 citation statements)

References 102 publications

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“…Section reviews ring-opening and ring-expansion reactions of oxetanes, where the four-membered ring is modified to generate new structural types. Readers are also directed to other notable and complementary reviews incorporating varied aspects of oxetane chemistry from Carreira and co-workers, , Abe, D’Auria and Racioppi, De Kimpe and co-workers, Mahal, Malapit and Howell, Sun and co-workers, and others. − The extensive use of oxetane motifs in other fields, including polymer chemistry as a monomer − and a cross-linker , and, for example, in catalytic reaction with CO 2 to generate cyclic carbonates, − , is outside the scope of this review and will not be considered. − …”

Section: Introductionmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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The four-membered oxetane ring has been increasingly exploited for its contrasting behaviors: its influence on physicochemical properties as a stable motif in medicinal chemistry and its propensity to undergo ring-opening reactions as a synthetic intermediate. These applications have driven numerous studies into the synthesis of new oxetane derivatives. This review takes an overview of the literature for the synthesis of oxetane derivatives, concentrating on advances in the last five years up to the end of 2015. These methods are clustered by strategies for preparation of the ring and further derivatization of preformed oxetane-containing building blocks. Examples of the use of oxetanes in medicinal chemistry are reported, including a collation of oxetane derivatives appearing in recent patents for medicinal chemistry applications. Finally, examples of oxetane derivatives in ring-opening and ring-expansion reactions are described.

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Section: Introductionmentioning

confidence: 99%

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

et al. 2016

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“…Upon treatment of the desired isomer ( 36 ) with KO t- Bu at elevated temperature, elimination of the C9 primary iodide occurred to form a vinyl group. It is presumed that Williamson-etherification by displacement of the C15 iodide by the C12 hydroxyl yields oxetane intermediate 39 , , which gives alcohol 40 following elimination in an overall transposition of the C12 hydroxy group . Xishacorene B was accessed from 40 using a two-step sequence involving oxidation of the primary hydroxy group to aldehyde 41 (using pyridinium chlorochromate) followed by Horner–Wadsworth–Emmons olefination with phosphonate 42 .…”

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confidence: 99%

Total Synthesis of (−)-Xishacorene B from (R)-Carvone Using a C–C Activation Strategy

2018

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The activation of C-C bonds that are traditionally viewed as unreactive, when coupled with other bond-forming processes, can offer new approaches to the synthesis of complex molecular scaffolds. In this Communication, we demonstrate the conversion of carvone to unusual bicyclo[3.3.1] and [3.2.1] frameworks by exploiting a Pd(0)-catalyzed C-C bond activation reaction and a radical cyclization process. This sequence is applied to a 10-step synthesis of the diterpene xishacorene B.

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“…Additionally, oxetanes are versatile building blocks of many other natural products and pharmaceutically active compounds [58]. Therefore, oxetanes have received a lot of interest as versatile precursors in synthetic chemistry [59,60].…”

Section: Oxetanesmentioning

confidence: 99%

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

Harmalkar

Choi

et al. 2019

Molecules

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Saturated oxygen heterocycles are widely found in a broad array of natural products and other biologically active molecules. In medicinal chemistry, small and medium rings are also important synthetic intermediates since they can undergo ring-opening and -expansion reactions. These applications have driven numerous studies on the synthesis of oxygen-containing heterocycles and considerable effort has been devoted toward the development of methods for the construction of saturated oxygen heterocycles. This paper provides an overview of the biological roles and synthetic strategies of saturated cyclic ethers, covering some of the most studied and newly discovered related natural products in recent years. This paper also reports several promising and newly developed synthetic methods, emphasizing 3–7 membered rings.

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Oxetanes as versatile building blocks in the total synthesis of natural products: An overview

Cited by 26 publications

References 102 publications

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry

Total Synthesis of (−)-Xishacorene B from (R)-Carvone Using a C–C Activation Strategy

An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies

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