Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion

Gholami, Hadi; Kulshrestha, Aman; Favor, Olivia K.; Staples, Richard J.; Borhan, Babak

doi:10.1002/ange.201900340

Cited by 9 publications

(6 citation statements)

References 52 publications

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“…Early on it was hypothesized that 13 and its congeners (16)(17)(18) shown in Fig. 4 were bacterial in origin as they shared similarities to chemical scaffolds of previously reported bacterial compounds including: saframycin A-C (19-21) from Streptomyces lavendulae [60,61], saframycin Mx1 (22) from Myxococcus xanthus [62], and safracin A and B (23,24) from Pseudomonas fluorescens [63]. In fact, safracin B (24) would later serve as the starting point in the semi-synthesis of Yondelis ® (13) for clinical use [64].…”

Section: Figmentioning

confidence: 99%

“…This action is similar to that of omuralide [21], a known inhibitor of proteasome which has structural similarities but important structural deficiencies for bioactivity vs. 2. (4) Even though many, somewhat lengthy, total syntheses have been published [22], a scale-up saline fermentation is being used to provide…”

Section: The Salinosporamide Story-from a Marine Actinomycete-derived...mentioning

confidence: 99%

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Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates

et al. 2020

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Marine-derived bacteria are a prolific source of a wide range of structurally diverse natural products. This review, dedicated to Professor William Fenical, begins by showcasing many seminal discoveries made at the University of California San Diego from marine-derived actinomycetes. Discussed early on is the 20-year journey of discovery and advancement of the seminal actinomycetes natural product salinosporamide A into Phase III anticancer clinical trials. There are many fascinating parallels discussed that were gleaned from the comparative literature of marine sponge, tunicate, and bacteria-derived natural products. Identifying bacterial biosynthetic machinery housed in sponge and tunicate holobionts through both cultureindependent and culture-dependent approaches is another important and expanding subject that is analyzed. Work reviewed herein also evaluates the hypotheses that many marine invertebrate-derived natural products are biosynthesised by associated or symbiotic bacteria. The insights and outcomes from metagenomic sequencing and synthetic biology to expand molecule discovery continue to provide exciting outcomes and they are predicted to be the source of the next generation of novel marine natural product chemical scaffolds.

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Section: Figmentioning

confidence: 99%

Section: The Salinosporamide Story-from a Marine Actinomycete-derived...mentioning

confidence: 99%

Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates

et al. 2020

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“…47 Recently total synthesis for salinosporamide A molecule has been reported. 46,48,49 2.11. Bromotyrosine alkaloid Several psammaplysin derivatives were obtained from the Indonesian marine sponge Aplysinella strongylata (Aplysinellidae).…”

Section: Salinosporamidementioning

confidence: 99%

Marine organisms as potential sources of natural products for the prevention and treatment of malaria

2023

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“…A safer but less reactive version of diazomethane, trimethylsilyldiazomethane, has also been applied to late-stage diversification. [19] Despite being less explosive, it must still be handled cautiously due to its acute toxicity. [20,21] Recently an impressive in situ batch method based on the hydrolysis of the imidazotetrazine drug molecule, temozolomide, was disclosed.…”

Section: Introductionmentioning

confidence: 99%

A Base‐Free, Low Temperature Click and Release Reaction for the In Situ Generation of Diazomethane

et al. 2023

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Diazomethane is a powerful reagent for numerous chemical reactions such as esterifications and the homologation of carboxylic acids. Unfortunately, the synthetic utility of diazomethane is severely limited by its toxicity and highly explosive nature. Diazald® is typically used for ex situ synthesis, however it requires cumbersome and hazardous transfer of diazomethane from a caustic aqueous phase to the reaction medium. Herein, we present a low temperature and base‐free in situ synthesis of diazomethane via a “click and release” reaction between an enamine and sulfonyl azide. Its utility is exemplified by the synthesis of diverse methyl esters in yields of up to 93%. Moreover, diazoketone synthesis from in situ generated diazomethane and acid chlorides was demonstrated for the first time. Finally, trideuteromethylation was achieved using acetone‐d6 as the deuterium source. We anticipate that this method will enable the safer use of diazomethane in organic synthesis and drug discovery programs.

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Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion

Cited by 9 publications

References 52 publications

Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates

Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates

Marine organisms as potential sources of natural products for the prevention and treatment of malaria

A Base‐Free, Low Temperature Click and Release Reaction for the In Situ Generation of Diazomethane

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