Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

Drew, Samuel L; Lawrence, Andrew L.; Sherburn, Michael S.

doi:10.1039/c5sc00794a

Cited by 40 publications

(21 citation statements)

References 47 publications

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“… 503 , 516 , 521 A related radical cation Diels–Alder approach has also been utilized in the synthesis of (±)-kingianic acid E ( 639 ) ( Scheme 110 ). 522 …”

Section: Visible-light Photoredox Catalysis—single-electron Transfer mentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

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“… 503 , 516 , 521 A related radical cation Diels–Alder approach has also been utilized in the synthesis of (±)-kingianic acid E ( 639 ) ( Scheme 110 ). 522 …”

Section: Visible-light Photoredox Catalysis—single-electron Transfer mentioning

confidence: 99%

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

2016

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“…More recently, Sherburn and coworkers demonstrated that (Z,Z,Z,Z)-tetraenes can also undergo the pericyclic cascade to produce endiandric acids, though only at elevated temperatures. [9][10][11] The impressive biomimetic syntheses by Nicolaou and Sherburn relied upon cis-selective reductions of conjugated alkynes (diynes or tetraynes) to generate octatetraene intermediates and trigger 8π/6π electrocyclization cascades. We sought to develop a concise and modular approach to endiandric acid derivatives with both fused and bridged tetracycles by exploring an alternate route to the 8π/6π electrocyclization cascade.…”

Section: Introductionmentioning

confidence: 99%

Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling

Wetzler

Kim

et al. 2016

Tetrahedron

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on the occasion of his receiving the Tetrahedron Young Investigator Award Both fused and bridged tetracyclic scaffolds characteristic of endiandric acid-type natural products have been prepared in just seven steps each (longest linear sequence) from Burke's commercial cis-2-bromovinylboronic acid MIDA ester. Three iterative Suzuki-Miyaura couplings using MIDA boronates, including the first such example of a Z-Z coupling, trigger an 8/6-electrocyclization cascade. The mixture of endo and exo bicycles thus formed are elaborated into tetracycles via Horner-Wadsworth-Emmons and Diels-Alder reactions. In the process, the endo and exo diastereomers interconvert to ultimately deliver the desired products.

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“…[116] Unfortunately, direct lithation of TMS protected precursor 358 led to decomposition. [116] Unfortunately, direct lithation of TMS protected precursor 358 led to decomposition.…”

Section: Transformations Of Terminal and Trialkylsilyl Protected Polymentioning

confidence: 99%

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

2019

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Polyynes are linear carbon rods that may be regarded as models of carbyne – still elusive linear allotropic form of carbon. This microreview addresses the use of polyynes as synthetic precursors of complex organic and organometallic compounds. Application of such unusual molecules as starting materials for various chemical transformations leads to products which often are not easily accessible using “traditional“ approaches. Polyynes may for instance be used in the synthesis of molecular wires, materials possessing high nonlinear optical response, complex donor–acceptor systems, solvatochromic fluorescent dyes or natural products. The most significant challenge here is to control the regioselectivity of a transformation of such linear sp‐hybridized carbon chains. The impact of steric and electronic properties of reagents on the reaction pattern is hence highly important and will be discussed. Moreover, the transformations of end‐groups will also be addressed since their reactivity might very often be different than that of acetylenes.

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Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F

Abstract: A measure of the strength of a synthetic strategy is its versatility: specifically, whether it allows structurally distinct targets to be prepared. This work describes the total synthesis of natural products of three distinct structural types from a common intermediate.

Cited by 40 publications

References 47 publications

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Concise, diastereoconvergent synthesis of endiandric-type tetracycles by iterative cross coupling

Reactivity of Polyynes: Complex Molecules from Simple Carbon Rods

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