Studies towards the total synthesis of Phostriecin

Kumar, Gavireddy Chaithanya; Muralikrishna, Katta; Satyanarayana, Vavilapalli; Kumar, Chintakrinda Suresh; Yadav, J. S.

doi:10.1016/j.tetlet.2017.12.068

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…[25] It proceeded via the dibromoolefin 25 and a Fritsch-Buttenberg-Wiechert rearrangement to the enyne 14. [26] We tried in vain to Scheme 2. Retrosynthetic analyses of the (polyenoyl)tetramic acids pyranonigrin J [(S)-3] and pyranonigrin I [(S)-4].…”

Section: Resultsmentioning

confidence: 99%

“…The commercially available α,β‐unsaturated aldehyde 16 was subjected to the sequence known as Corey‐Fuchs’ [25] . It proceeded via the dibromoolefin 25 and a Fritsch‐Buttenberg‐Wiechert rearrangement to the enyne 14 [26] . We tried in vain to hydro(tributylstannylate) its C≡C bond such that the C−Sn‐bond formed only at C‐1 (→ desired stannane 13 ) without competing at C‐2 (→ undesired stannane iso ‐ 13 ): A 67 : 33 mixture of 13 and iso ‐ 13 resulted when 14 reacted with HSnBu 3 and cat.…”

Section: Resultsmentioning

confidence: 99%

“…[22] footnote [11]. Their specific rotations [8] {[α] D 26 = À 227.8 (c = 0.05 in MeOH) and [α] D 26 = À 316 (c = 0.2 in MeOH), respectively} in conjunction with the now-certain (S)-configurations of the equally levorotatory pyranonigrins I (4) and J (3) make it likely that the terreones D and E are (S)-configured as well.…”

Section: Discussionmentioning

confidence: 99%

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Structure‐Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

Drescher

Brückner

2022

Eur J Org Chem

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The polyenoyltetramic acids pyranonigrin J (3) and pyranonigrin I (4) had been isolated from Aspergillus niger. Their origins from and roles in biosynthesis as well as the S-configurations of their stereocenter had been deduced from expression experiments with modifications of the corresponding gene cluster. We corroborated this stereochemical assignment after executing the first total syntheses of both compounds because they had essentially the same specific rotations as their natural counterparts. Our syntheses used the β-ketothioester 18 as a conjunctive reagent. It was combined with the l-serine derivatives (S)-19 or (S)-21 ("Western building blocks"), respectively, through aminolyses. Stille couplings with the stannane 13 ("Eastern building block") followed. The resulting β-ketoamides (S)-11 and (S)-12 underwent desilylative Lacey-Dieckmann cyclizations when exposed to 8 equiv. of Bu 4 NF. They rendered the polyenoyltetramic acids (S)-26 [acidolysis: ! (S)-3] and (S)-4, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Structure‐Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

Drescher

Brückner

2022

Eur J Org Chem

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Studies towards the Synthesis of Portentol

et al. 2018

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Six-Membered Ring Systems: With O and/or S Atoms

Santos¹,

Silva²

2020

Progress in Heterocyclic Chemistry

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This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein). NoticesKnowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

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Studies towards the total synthesis of Phostriecin

Cited by 6 publications

References 27 publications

Structure‐Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

Structure‐Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

Studies towards the Synthesis of Portentol

Six-Membered Ring Systems: With O and/or S Atoms

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