Toward the Synthesis of the Antibiotic Branimycin: Novel Approaches to Highly Substituted <i>cis</i>‐Decalin Systems

Mulzer, Johann; Castagnolo, Daniele; Felzmann, Wolfgang; Marchart, Stefan; Pilger, Christian; Enev, Valentin S.

doi:10.1002/chem.200600279

Cited by 20 publications

(8 citation statements)

References 34 publications

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“…A follow‐up investigation of the synthesis of the decaline core was published by Mulzer, with the first total synthesis of branimycin achieved in 2010 …”

Section: Applications To Total Synthesis Of Natural Productsmentioning

confidence: 99%

Applications of the Wittig–Still Rearrangement in Organic Synthesis

Rýček

Hudlický

2017

Angew Chem Int Ed

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This Review traces the discovery of the Wittig-Still rearrangement and its applications in organic synthesis. Its relationship to Wittig rearrangements is discussed along with detailed analysis of E/Z- and diastereoselectivity. Modifications of the products arising from the Wittig-Still rearrangement are reviewed in the context of increased complexity in intermediates potentially useful in target-oriented synthesis. Early applications of the Wittig-Still rearrangement to modifications of steroids are reviewed as are applications to various terpene and alkaloid natural product targets and miscellaneous compounds. To the best of our knowledge, the literature is covered through December 2016.

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“…A follow‐up investigation of the synthesis of the decaline core was published by Mulzer, with the first total synthesis of branimycin achieved in 2010 …”

Section: Applications To Total Synthesis Of Natural Productsmentioning

confidence: 99%

Applications of the Wittig–Still Rearrangement in Organic Synthesis

Rýček

Hudlický

2017

Angew Chem Int Ed

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“…Fused isoxazoles or isoxazolines obtained by the INOC reaction may also serve as synthetically important intermediates for many biologically active compounds. Such compounds, including the HBV inhibitor entecavir [19,20], the antibiotic branimycin [21], the antiviral (+)-Brefeldin A [22], tricyclic isoxazoles combining serotonin (5-HT) reuptake inhibition with α 2 -adrenoceptor blocking activity [23] and the alkaloids meliacarpinin B [24] and Palhinine A [25], have been synthesized by employing INOC as a key step.…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazoles via Intramolecular Nitrile Oxide Cycloaddition

et al. 2021

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A simple and efficient synthetic route to the novel 3a,4-dihydro-3H,7H- and 4H,7H-pyrazolo[4′,3′:5,6]pyrano[4,3-c][1,2]oxazole ring systems from 3-(prop-2-en-1-yloxy)- or 3-(prop-2-yn-1-yloxy)-1H-pyrazole-4-carbaldehyde oximes has been developed by employing the intramolecular nitrile oxide cycloaddition (INOC) reaction as the key step. The configuration of intermediate aldoximes was unambiguously determined using NOESY experimental data and comparison of the magnitudes of 1JCH coupling constants of the iminyl moiety, which were greater by approximately 13 Hz for the predominant syn isomer. The structures of the obtained heterocyclic products were confirmed by detailed 1H, 13C and 15N NMR spectroscopic experiments and HRMS measurements.

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“…In keeping with the retrosynthetic plan outlined previously,6c we intended to assemble the target molecule by the addition of the organometallic side chain 3 to the cis ‐decalin ketone 2 (Scheme ). We recently described6g the preparation of enantiopure decalin 5 by the desymmetrization of precursor 4 (Scheme ).…”

Section: Methodsmentioning

confidence: 99%