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

Go, Eun Bin; Wetzler, Shannon P.; Kim, Lee Joon; Chang, Arthur; Vosburg, David A.

doi:10.1016/j.tet.2016.02.040

Cited by 14 publications

(11 citation statements)

References 20 publications

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“…This tetraene was primed for an 8π/6π electrocylization cascade to generate a fused 4-6 ring system, which led to the completion of cryptobeilic acid D after some additional final steps (Figure 7g). 176 …”

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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“…[84,91,92,93,94] This platform leverages the capacity of the trivalent MIDA-ligand to reversibly block the reactivity of a boronic acid via rehybridization of the boron center from sp 2 to sp 3 . The MIDA ligand can also be removed under aqueous or mild aqueous basic conditions which reveals the free boronic acid.…”

Section: One Machine – Many Small Moleculesmentioning

confidence: 99%

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

2018

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The eighteenth and nineteenth centuries marked a sweeping transition from manual to automated manufacturing on the macroscopic scale. This enabled an unmatched period of human innovation that helped drive the Industrial Revolution. The impact on society was transformative, ultimately yielding substantial improvements in living conditions and lifespan in many parts of the world. During the same time period, the first manual syntheses of organic molecules was achieved. Now, two centuries later, we are poised for an analogous transition from highly customized crafting of specific molecular targets by hand to the increasingly general and automated assembly of many different types of molecules with the push of a button. Automation of customized small molecule synthesis pathways is already enabling safer, more reproducible, and readily scalable production of specific targets, and general machines now exist for the synthesis of a wide range of different peptides, oligonucleotides, and oligosaccharides. Creating general machines that are similarly capable of making many different types of small molecules on-demand, akin to that which has been achieved on the macroscopic scale with 3D printers, has proven to be substantially more challenging. Yet important progress is being made toward this potentially transformative objective with two complementary approaches: (1) automation of customized synthesis routes to different targets via machines that enable use of many different reactions and starting materials, and (2) automation of generalized platforms that make many different targets using common coupling chemistry and building blocks. Continued progress in these exciting directions has the potential to shift the bottleneck in molecular innovation from synthesis to imagination, and thereby help drive a new industrial revolution on the molecular scale.

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“…On the other hand SMCR of bromide 331 with boronate 334 afforded dienyl MIDA boronate 335 in a smilar maner. Compunds 333 and 335 were successfully converted into the corresponding natural products 329 and 330 respectively after several steps (Scheme ) …”

Section: Coupling Of Sp2 Hybridized C–b Compoundsmentioning

confidence: 99%

“…Compunds 333 and 335 were successfully converted into the corresponding natural products 329 and 330 respectively after several steps (Scheme 56). [181] Altenuic acid III 338 was initially extracted along with Altenuic acids I and II which is a toxin produced by SCHEME Alternaria tenuis. [182] The structure of the mycotoxin Altenuic acid III 336 has been determined.…”

Section: Hamigeran Bmentioning

confidence: 99%

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

Koshvandi

Heravi

Momeni

2018

Applied Organom Chemis

168

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Suzuki‐Miyaura Coupling Reaction (SMCR) has been extensively used in the total synthesis of natural products. We underscored these achievements in a report published in Tetrahedron up to 2012. Since then, there has been tremendous growth in this field and numerous articles have been published after 2012. In this review, we tried to go insight and highlight the current developments in the applications of SMCR as a key and strategic step (steps) in the total synthesis of biologically active natural products accomplished and reported from 2012 till date.

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

Cited by 14 publications

References 20 publications

Towards the generalized iterative synthesis of small molecules

Towards the generalized iterative synthesis of small molecules

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

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