Concise Total Synthesis of (−)‐Myxalamide A

Fujita, Kazuhiro; Matsui, Ryosuke; Suzuki, Takahiro; Kobayashi, Susumu

doi:10.1002/anie.201203093

Cited by 48 publications

(21 citation statements)

References 61 publications

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“…MIDA boronates are also convenient to prepare, analyze, purify, and store and more than 170 are now commercially available. 24 Collectively, these features have enabled the simple, efficient, and flexible synthesis of a wide range of small molecule natural products, 21,23,25-30 pharmaceutical agents, 31-34 ligands, 35,36 and materials 37 via iterative cross-coupling.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction

2014

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The inherent modularity of polypeptides, oligonucleotides, and oligosaccharides has been harnessed to achieve generalized building block-based synthesis platforms. Importantly, like these other targets, most small molecule natural products are biosynthesized via iterative coupling of bifunctional building blocks. This suggests that many small molecules also possess inherent modularity commensurate with systematic building block-based construction. Supporting this hypothesis, here we report that the polyene motifs found in >75% of all known polyene natural products can be synthesized using just 12 building blocks and one coupling reaction. Using the same general retrosynthetic algorithm and reaction conditions, this platform enabled the synthesis of a wide range of polyene frameworks covering all of this natural product chemical space, and first total syntheses of the polyene natural products asnipyrone B, physarigin A, and neurosporaxanthin β-D-glucopyranoside. Collectively, these results suggest the potential for a more generalized approach for making small molecules in the laboratory.

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Section: Introductionmentioning

confidence: 99%

Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction

2014

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“…171 A key challenge in this synthesis was construction of the central trans-trans-cis-trans tetraene, as such motifs are difficult to install in a stereocontrolled fashion. 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.…”

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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“…7 An elegant example of such a tactic is the development by Burke of an assembly of so-called MIDA-boronate building blocks, that allow the deployment of iterative cross-couplings en route to polyenic natural products. 8 Nevertheless, the syntheses of the basic mono-olefinic fragments are typically multi-step and mandate the introduction of a halide and organometallic residue in each fragment. We report herein a strategy for the direct preparation of dienyl carboxylate building blocks that significantly streamlines the total synthesis of polyene natural products.…”

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confidence: 99%