Biomimetically Inspired Synthesis of Exotine A

Lepovitz, Lance T; Martin, Stephen F.

doi:10.1021/acs.orglett.8b03423

Cited by 8 publications

(5 citation statements)

References 26 publications

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“…Martin and co‐workers [27a] designed a novel synthesis of Exotin A 19.1 via reactions of prenal and trans ‐dehydroosthol. This acid‐promoted protocol would deliver Exotine A 19.1 and 11’ ‐epi ‐Exotine A 19.2 (Scheme 19).…”

Section: Nucleophilic C3mentioning

confidence: 99%

“…Indoles are extremely important because of their biological activities. Besides, they were utilized in total synthesis of natural products, such as Spirobacillene A, [1a] Exotine A, [1b] (−)‐Isatisine A, [1c] (+)‐Okaramine [1d] . Well‐known drugs like sumatriptan, tadalafil, fluvastatin and rizatriptan all contains indole frameworks [1e] .…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances of Three‐component Reactions of Simple Indoles

et al. 2022

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Indoles are extremely important and versatile building blocks in the field of chemistry. This review highlights the advance made in the three-component reactions of indoles between 2011-2021. The reaction types are classified into three categories based on the trigger mechanisms.Reactions with alkenes, alkynes, aldehydes, imines, ketones, S, Se, etc are discussed. In order to highlight the mechanisms involved, this review has provided specific analysis inside a gray box in each scheme. We hope these studies will promote future research in the indole area.

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Section: Nucleophilic C3mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances of Three‐component Reactions of Simple Indoles

et al. 2022

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“…The substituted indole nucleus is prevalent in numerous natural products and is extremely important, while the synthetic methodology for direct indole functionalizations is of great significance [1–2] . Indoles have wide applications in the organic synthesis and were utilized in total synthesis [1l,r] of natural products like Spirobacillene A, [2a] Exotine A, [2b] (−)‐Isatisine A, [2c] (+)‐Okaramine [2d] . Besides, the molecular structures of well‐known drugs such as sumatriptan, tadalafil, fluvastatin and rizatriptan are based on indole frameworks [2e] .…”

Section: Introductionmentioning

confidence: 99%

Recent Studies of Bifunctionalization of Simple Indoles

Wang

et al. 2021

Asian J Org Chem

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Indole structures are extremely important and widely employed in organic synthesis. This review will focus on direct bifunctionalizations of simple indoles in tandem reactions. Recent studies have been divided into four types by trigger mechanisms: (1) nucleophilic C3; (2) nucleophilic NH for cyclization; (3) reduction; (4) oxidation. Reactions with carbocations, pyridines, alkenes, alkynes, aldehydes, imines, halogenated compounds et al were discussed. We hope this review will promote future research in the use of indoles.

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“…Although they briefly examined the use of prenal ( 15 ) instead of 21 as the aldehyde component in this 3CR, no exotine B ( 2 ) or any other cyclohepta[ b ]indole was observed. We were unaware of these efforts when we embarked upon our studies, and we now report the details of our syntheses of exotine A ( 1 ), preliminary details of which were published, and exotine B ( 2 ) according to the biomimetically inspired process summarized in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Biomimetically Inspired, One-Step Synthesis of Exotine A and Exotine B

Lepovitz

Martin

2020

J. Org. Chem.

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The one-step syntheses of exotine A and exotine B, which comprise the unusual coumarin-cyclohepta[b]indole ring system, have been achieved via the biomimetically inspired combination of indole, prenal, and either trans-dehydroosthol or gleinadiene. This facile threecomponent reaction delivered a mixture (17:1) of exotine A and 11′-epiexotine A in a 43% yield from trans-dehydroosthol and a mixture (4:1) of exotine B and 11′-epi-exotine B in a 50% yield from gleinadiene. Some mechanistic aspects of this process were explored, and spectral evidence for 3,3′-spiroindolenine intermediates was obtained. Moreover, a skeletal isomer of exotine A that likely originates from a 1,2-alkyl rearrangement of a protonated 3,3′-spiroindolenine was isolated and characterized by Xray crystallography. These findings not only provide experimental support for Jiang's proposed biosynthesis of exotine A and exotine B but also foreshadow the existence of other exotine-derived natural products having isomeric frameworks. Exploratory attempts to induce an enantioselective 3CR using a chiral phosphoric acid were unsuccessful.

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Biomimetically Inspired Synthesis of Exotine A

Cited by 8 publications

References 26 publications

Recent Advances of Three‐component Reactions of Simple Indoles

Recent Advances of Three‐component Reactions of Simple Indoles

Recent Studies of Bifunctionalization of Simple Indoles

Biomimetically Inspired, One-Step Synthesis of Exotine A and Exotine B

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