Enantioselective Total Synthesis of Plectosphaeroic Acid B

Jabri, Salman; Overman, Larry E.

doi:10.1021/ja401423j

Cited by 37 publications

(19 citation statements)

References 55 publications

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“…Overman and co‐workers employed the same strategy in the synthesis of (+)‐gliocladine C and oxygen was used instead of iodine as the sole oxidant (Scheme ) 31. Very recently, in the synthesis of di(methylthio)ethers of plectosphaeroic acid B by Jabri and Overman, 80–90 % yields were obtained under the conditions of hydrogen sulfide/BF 3 ⋅ Et 2 O, followed by methyl iodide/potassium carbonate (Scheme ) 32…”

Section: Cs Bond Construction By Different Sulfuration Agentsmentioning

confidence: 99%

Transfer of Sulfur: From Simple to Diverse

Liu

Jiang

2013

Chemistry An Asian Journal

561

146

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The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration agents have been developed for thionation reactions over the past few decades. In this Focus Review, we collect and summarize the C-S bond-formation reactions that have been used to construct C-S bonds in natural products and pharmaceutical compounds.

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Section: Cs Bond Construction By Different Sulfuration Agentsmentioning

confidence: 99%

Transfer of Sulfur: From Simple to Diverse

Liu

Jiang

2013

Chemistry An Asian Journal

561

146

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“…published total syntheses of gliotoxin ( 4 ), gliotoxin G, emethallicin E, and haematocin 4. Recently, a total synthesis of plectosphaeroic acid B was accomplished by Overman et al 14. Most of the above‐named compounds contain indole or indoline moieties.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Highly Functionalized Hydroindoles as Building Blocks for Rostratins B–D and Synthesis of the Pentacyclic Core of Rostratin C

Zhong

Sauter

Nieger

et al. 2015

Chemistry A European J

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The stereoselective synthesis of a variety of functionalized hydroindoles suitable as building blocks for thiodiketopiperazine natural products such as rostratins B-D is reported. The key precursor for all transformations is a previously reported hexahydroindole compound. All functional groups were installed with the desired stereochemistry and the feasibility of the synthetic strategy was exemplified by dimerization of two hydroindole units to form the pentacyclic C2 -symmetric scaffold of rostratin C.

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“…[14,15] At ransition-metal-catalyzed CÀNc oupling with a5 -functionalized arene [16] was put aside in favor of am etal-free system to avoid catalyst scavenging operations,w hich can be harmful toc omplexa nd unstable molecules. However,i nstead of incorporating the original mono-protected aminoresorcinol, we soughtt o utilize ab uilding block that would remain stable as the aniline free base with no protecting group.…”

mentioning

confidence: 99%

Highly Efficient Synthesis of a Staphylococcus aureus Targeting Payload to Enable the First Antibody–Antibiotic Conjugate

Linghu¹,

Segraves²,

Abramovich³

et al. 2017

Chemistry A European J

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A practical synthesis of the complex payload for an anti-Staphylococcus aureus THIOMAB antibody-antibiotic conjugate (TAC) is described. The route takes advantage of a delicate oxidative condensation, achieved using a semi-continuous flow procedure. It allows for the generation of kilogram quantities of a key intermediate to enable a mild nucleophilic aromatic substitution to the tertiary amine free drug. The linker component is introduced as a benzylic chloride, which allows formation of the quaternary ammonium salt linker-drug. This chemical process surmounts numerous synthetic challenges and navigates deeply colored and unstable compounds to support clinical studies to counter S. aureus bacterial infections.

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Enantioselective Total Synthesis of Plectosphaeroic Acid B

Abstract: The first total synthesis of a member of the plectosphaeroic acid family of fungal natural products is reported. Key steps include the late-stage formation of the hindered N6–C9″ bond and stereoselective introduction of the two methylthio substituents.

Cited by 37 publications

References 55 publications

Transfer of Sulfur: From Simple to Diverse

Transfer of Sulfur: From Simple to Diverse

Stereoselective Synthesis of Highly Functionalized Hydroindoles as Building Blocks for Rostratins B–D and Synthesis of the Pentacyclic Core of Rostratin C

Highly Efficient Synthesis of a Staphylococcus aureus Targeting Payload to Enable the First Antibody–Antibiotic Conjugate

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