Total Synthesis of the Antibiotic Elansolid B1

Weber, A.; Dehn, Richard; Schläger, Nadin; Dieter, Bastian; Kirschning, Andreas

doi:10.1021/ol403441c

Cited by 29 publications

(37 citation statements)

References 32 publications

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“…The preparation of the newly modified western fragment started from known IMDA product 9 [7], which was first reduced at C-25 (Scheme 3). The two diastereoisomers could be separated by chromatography and the stereochemical assignment of the major isomer was based on X-ray crystallographic analysis [7].…”

Section: Resultsmentioning

confidence: 99%

“…The two diastereoisomers could be separated by chromatography and the stereochemical assignment of the major isomer was based on X-ray crystallographic analysis [7]. Next, Tamao–Fleming oxidation [10] yielded phenol 15 .…”

Section: Resultsmentioning

confidence: 99%

“…Dry solvents were obtained after filtration through drying columns on a M. Braun solvent purification system or purchased form commercial providers. The synthesis of building blocks 9 [7] and 12 [9] was reported before.…”

Section: Methodsmentioning

confidence: 99%

“…For the first generation total synthesis of elansolid B1 ( 2 ) we utilized an endo -selective intramolecular Diels–Alder (IMDA) cycloaddition as key step to construct the tetrahydroindane unit (Scheme 1) [7]. An enone, derived from allylic alcohol 8 served as precursor to yield tetrahydroindane 9 with excellent diastereocontrol at −25 °C.…”

Section: Introductionmentioning

confidence: 99%

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Total synthesis of elansolids B1 and B2

Wang¹,

Kirschning²

2017

Beilstein J. Org. Chem.

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The elansolids A1–A3, B1, and B2 are secondary metabolites formed by the gliding bacterium Chitinophaga sancti. They show antibacterial activity against Gram-positive bacteria. A second generation total synthesis of the antibiotic elansolid B1 (2) and the first synthesis of elansolid B2 (3) are reported. In contrast to previous work, the (Z,E,Z)-triene at C10–C15 was assembled by using an optimized C–C cross-coupling sequence with a Suzuki cross-coupling reaction as key step.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Total synthesis of elansolids B1 and B2

Wang¹,

Kirschning²

2017

Beilstein J. Org. Chem.

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“…For example, MIDA boronates have enabled the syntheses of (−)-aurantioclavine 22 via slow-release cross-coupling, 23 as well as elansolid B1, 24 (−)-myxalamide A, 25 eicosapentaenoate methyl ester, 26 marinoquinoline C and E, 27 and in other applications. 28 …”

Section: Accessing Linear Csp2-rich Small Molecules Via Iterativementioning

confidence: 99%

From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks

2015

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Small molecules can powerfully benefit society, but the study and optimization of their function is too often impeded by the time-intensive and specialist-dependent process that is typically used to make them. In contrast, general and automated platforms have been developed for peptide, oligonucleotide, and increasingly oligosaccharide synthesis, resulting in on-demand access to these molecules, even for non-specialists. A more generalized and automated approach for making small molecules could similarly help shift the rate limiting step in small molecule science from synthesis to function. Targeting this goal, we have developed a fully automated and increasingly general platform for iterative coupling of boronate building blocks. Analogous to peptide synthesis, the process involves iterative coupling of haloboronic acids protected as the corresponding N-methyliminodiacetic acid (MIDA) boronates. This platform has enabled us and other groups to access many polyene natural products, including the polyene motifs in >75% of all polyene natural products. It further allowed us to derivatize and thereby understand the powerful but also highly toxic antifungal natural product amphotericin B, which has led to the development of less toxic derivatives currently under evaluation as drug candidates. We also discovered a stereocontrolled entry into chiral, non-racemic α-boryl aldehydes, which are versatile intermediates for the synthesis of many Csp3 boronate building blocks that are otherwise difficult to access. We have also expanded the scope of the platform to include Csp3-rich, polycyclic molecules using a linear-to-cyclized strategy, in which Csp3 boronate building blocks are iteratively assembled into linear precursors that are then cyclized into the cyclic frameworks found in many natural products and natural product-like structures. Enabled by the serendipitous discovery of a catch-and-release protocol for generally purifying MIDA boronate intermediates, the platform has been automated. The synthesis of 14 distinct classes of small molecules, including pharmaceuticals, materials, and polycyclic natural products has been achieved using this new synthesis machine. It is anticipated that the scope of small molecules accessible by this platform will continue to expand via further developments in building block synthesis, Csp3 cross-coupling methodologies, and cyclization strategies.

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A Half Century of the Sonogashira Reaction

Frankenberger,

Wendinger,

Scherer

et al. 2025

Organic Reactions

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Conjugated alkynes are valuable intermediates in the synthesis of natural products, agrochemicals, pharmaceuticals, fine chemicals, and organic molecular materials. Since its introduction in 1975, the palladium‐catalyzed Sonogashira reaction has become the primary choice for the construction of sp–sp 2 carbon–carbon bonds in aryl‐, heteroaryl‐, and alkenyl‐substituted alkynes. A vast range of reaction conditions have been explored to expand and optimize the scope of the Sonogashira reaction, including sustainable variants, microwave‐assisted cross couplings, and cross couplings performed in water. Research efforts also target the development of improved catalytic systems for the Sonogashira reaction, such as solid‐supported palladium catalysts and nanoparticles, the use of N ‐heterocyclic carbenes (NHCs) as ligands, as well as copper‐free variants of the reaction. This Chapter reviews the application of the palladium‐catalyzed Sonogashira cross coupling of terminal alkynes with aryl or alkenyl halides and triflates. Coupling reactions that form conjugated alkynes via alternative methods, or use different electrophiles, catalysts, or alkynes, are also briefly described.

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Total Synthesis of the Antibiotic Elansolid B1

Cited by 29 publications

References 32 publications

Total synthesis of elansolids B1 and B2

Total synthesis of elansolids B1 and B2

From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks

A Half Century of the Sonogashira Reaction

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