Application of Ring Closing Metathesis to the First Total Synthesis of (<i>R</i>)-(+)-Muscopyridine:  Determination of Absolute Stereochemistry

Hagiwara, Hisahiro; Katsumi, Tatsuya; Kamat, Vijayendra P.; Hoshi, Takashi; Suzuki, Toshio; Ando, Masayoshi

doi:10.1021/jo000785r

Cited by 25 publications

(9 citation statements)

References 20 publications

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“…au, glessene@wehi.edu.au † Electronic supplementary information (ESI) available: Experimental procedures; copies of 1 H and13 C NMR spectra; references. See DOI: 10.1039/c0ob00723d Scheme 1 Retrosynthesis of constrained mimetics 2.…”

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confidence: 99%

Benzoylureas as removable cisamide inducers: synthesis of cyclic amidesviaring closing metathesis (RCM)

et al. 2011

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Rapid and high yielding synthesis of medium ring lactams was made possible through the use of a benzoylurea auxiliary that serves to stabilize a cisoid amide conformation, facilitating cyclization. The auxiliary is released after activation under the mild conditions required to deprotect a primary amine, such as acidolysis of a Boc group in the examples given here. This methodology is a promising tool for the synthesis of medium ring lactams, macrocyclic natural products and peptides.

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confidence: 99%

Benzoylureas as removable cisamide inducers: synthesis of cyclic amidesviaring closing metathesis (RCM)

et al. 2011

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“…Hagiwara and co-workers [ 173 ] have synthesized muscopyridine starting with methyl acetoacetate ( 231 ). They treated 231 with 5-bromo-1-pentene to generate keto ester 232 (60%).…”

Section: Reviewmentioning

confidence: 99%

Selected synthetic strategies to cyclophanes

Kotha¹,

Shirbhate²,

Waghule³

2015

Beilstein J. Org. Chem.

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SummaryIn this review we cover various approaches to meta- and paracyclophanes involving popular reactions. Generally, we have included a strategy where the reaction was used for assembling the cyclophane skeleton for further functionalization. In several instances, after the cyclophane is made several popular reactions are used and these are not covered here. We included various natural products related to cyclophanes. To keep the length of the review at a manageable level the literature related to orthocyclophanes was not included.

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“…The next step, the ester saponification with subsequent decarboxylation, required tedious optimization. After unsatisfying experimentation with several alternative procedures (see the Supporting Information for details), we finally succeeded with a modified Krapcho protocol in DMPU which followed some literature precedence . The yield (61%) was moderate, but the starting material could be recovered (i.e., 99% based on recovered starting material (brsm)).…”

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Improved and Flexible Synthetic Access to the Spiroindole Backbone of Cebranopadol

2020

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By changing the dimethylamino to a nitro group, a novel synthetic access to the spirocyclic opioid analgesic cebranopadol was developed that is much more efficient compared with the established route. On the basis of the α-acidity of α-nitrotoluene, the two-fold Michael addition to acrylate gave an acyclic precursor compound, which was easily transformed by Dieckmann condensation and decarboxylation to the cyclohexanone derivative needed for the annulation of the indole ring by an oxa-Pictet–Spengler reaction. As an additional benefit, the reduction of the nitro group furnished an amine, which could be late-stage-diversified to carboxamides, sulfonamides, ureas, and N-alkyl congeners. The transformation of the nitro group at the spirocyclic scaffold to the dimethylamino function of the actual title compound was achieved in one step with zinc/formic acid/formaldehyde in 83% yield.

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Application of Ring Closing Metathesis to the First Total Synthesis of (R)-(+)-Muscopyridine: Determination of Absolute Stereochemistry

Cited by 25 publications

References 20 publications

Benzoylureas as removable cisamide inducers: synthesis of cyclic amidesviaring closing metathesis (RCM)

Benzoylureas as removable cisamide inducers: synthesis of cyclic amidesviaring closing metathesis (RCM)

Selected synthetic strategies to cyclophanes

Improved and Flexible Synthetic Access to the Spiroindole Backbone of Cebranopadol

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