(Z)-(2-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Woerly, Eric M.; Struble, Justin R.; Palyam, Nagarjuna; O'Hara, Sean P.; Burke, Martin D.

doi:10.1016/j.tet.2011.04.021

Cited by 46 publications

(24 citation statements)

References 30 publications

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“…The capacity of olefinic stereochemical elements pre-installed in shelf-stable bifunctional MIDA boronate building blocks to be faithfully translated into growing targets by using mild and stereospecific cross-coupling methods simplifies this type of complex problem. 165–166, 179 Specifically in this case, a cis -bifunctional vinyl MIDA boronate building block was iteratively cross-coupled to unite the two key fragments of the polyene core of myxalamide A in a stereospecific fashion. Moreover, no protecting groups were required, as the cross-coupling reactions proceeded in the presence of two free alcohols.…”

Section: Iterative Cross-coupling With Mida Boronatesmentioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

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Small molecules have extensive untapped potential to benefit society, but access to this potential is too often restricted by limitations inherent to the customized approach currently used to synthesize this class of chemical matter. In contrast, the “building block approach”, i.e., generalized iterative assembly of interchangeable parts, has now proven to be a highly efficient and flexible way to construct things ranging all the way from skyscrapers to macromolecules to artificial intelligence algorithms. The structural redundancy found in many small molecules suggests that they possess a similar capacity for generalized building block-based construction. It is also encouraging that many customized iterative synthesis methods have been developed that improve access to specific classes of small molecules. There has also been substantial recent progress toward the iterative assembly of many different types of small molecules, including complex natural products, pharmaceuticals, biological probes, and materials, using common building blocks and coupling chemistry. Collectively, these advances suggest that a generalized building block approach for small molecule synthesis may be within reach.

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Section: Iterative Cross-coupling With Mida Boronatesmentioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

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“…The preparation of an analogous ( Z )-(2-bromovinyl)-MIDA boronate has been accomplished previously by Burke. 21 Following a similar strategy it was found that ( Z )-(2-chlorovinyl)-MIDA boronate could be synthesized efficiently in one step by treatment of commercially available 54 with iodine monochloride in the presence of 2,6-lutidine. The pure product could be easily isolated by precipitation from diethyl ether.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (−)-Deschloromytilipin A and (−)-Danicalipin A

Landry

McKenna

et al. 2016

J. Am. Chem. Soc.

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A titanium-based catalytic enantioselective dichlorination of simple allylic alcohols is described. This dichlorination reaction provides stereoselective access to all common dichloroalcohol building blocks used in syntheses of chlorosulfolipid natural products. An enantioselective synthesis of ent-(–)-deschloromytilipin A and a concise, eight-step synthesis of ent-(–)-danicalipin A are executed and employ the dichlorination reaction as the first step. Extension of this system to enantioselective dibromination and its use in the synthesis of pentabromide stereoarrays relevant to bromosufolipids is reported. The described dichlorination and di-bromination reactions are capable of exerting diastereocontrol in complex settings allowing X-ray crystal structure analysis of natural and unnatural diastereomers of polyhalogenated stereohexads.

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“…Recently, the generation of B–I triene 446 via two cycles of newly developed methodology (like in Scheme )—stereospecific Stille‐type coupling bis‐metalated olefin 202 with B–I bifunctionalized diene 444 and later stereoretentive iododegermylation—has been reported (Scheme ) …”

Section: Suzuki–miyaura Couplingmentioning

confidence: 99%

“…The obtained triene 446 is the key building block in the synthesis of polyenic frameworks (Scheme ). The synthetic sequence strategy based on the iterative cross‐coupling (ICC) was used to access the triene 446 applied as an intermediate in the total synthesis of light‐harvesting carotenoid (−)‐peridinin 450 which is a pigment associated with chlorophyll (Scheme ) …”

Section: Suzuki–miyaura Couplingmentioning

confidence: 99%

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

Pyziak

Walkowiak

Marciniec

2016

Chemistry A European J

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In the syntheses developed to access naturally occurring compounds, especially bioactive substances, boron-functionalized dienes (also "linchpin" reagents) are used as key reagents. Structurally unique dienes are found in nature, and play important biological and chemical roles. Recently, linchpin moieties have been proved as useful substrates for a variety of highly functionalized chemical transformations. The products of these processes are potentially of some use for the syntheses of an important class of natural products showing a wide range of biological activities. This review describes progress in the synthesis of borylsubstituted buta-1,3-dienes as well as their application in organic chemistry.

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(Z)-(2-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Cited by 46 publications

References 30 publications

Towards the generalized iterative synthesis of small molecules

Towards the generalized iterative synthesis of small molecules

Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (−)-Deschloromytilipin A and (−)-Danicalipin A

Recent Advances in Boron‐Substituted 1,3‐Dienes Chemistry: Synthesis and Application

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