A new approach to A/B ring analogue of eleutherobin and sarcodictyns through a sequence of highly diastereofaceselective Diels–Alder reaction and ring opening–ring closing metathesis (RO–RCM)

Malik, Chanchal K.; Hossain, Md. Firoj; Ghosh, Subrata

doi:10.1016/j.tetlet.2009.04.033

Cited by 17 publications

(2 citation statements)

References 37 publications

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“…Furthermore, the precursor of the A/B ring analog of the antitumor compounds eleutherobin 157 and sarcodictyns 158a,b (Fig. 9) was obtained by a diastereoselective Diels-Alder reaction of a dienophile containing a furanosugar moiety with cyclopentadiene followed by sequential ROM of the adduct 159 and RCM of the acrylate 160 affording lactone 161 (Scheme 53) [219].…”

Section: Nine-membered Lactonesmentioning

confidence: 99%

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Bassetti

D’Annibale

2015

Topics in Heterocyclic Chemistry

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Section: Nine-membered Lactonesmentioning

confidence: 99%

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Bassetti

D’Annibale

2015

Topics in Heterocyclic Chemistry

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“…To synthesize various aza-arenes and cyclic imines, such as quinolines, aza-spiro compounds and dihydropyrroles, the intramolecular S N 2-type reaction at the oxime nitrogen is useful [ 1 – 6 ]. Here, we plan to use the BR in combination with a ring-rearrangement metathesis (RRM) [ 7 – 24 ] to generate lactam derivative 1 . The RRM protocol involves a tandem process with several metathetic transformations such as ring-closing metathesis (RCM) and ring-opening metathesis (ROM).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps

Kotha¹,

Ravikumar²,

Majhi³

2015

Beilstein J. Org. Chem.

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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A new approach to A/B ring analogue of eleutherobin and sarcodictyns through a sequence of highly diastereofaceselective Diels–Alder reaction and ring opening–ring closing metathesis (RO–RCM)

Cited by 17 publications

References 37 publications

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Metathetic Synthesis of Common and Medium-Sized Lactones: The State of the Art

Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps

Olefin Ring‐Closing Metathesis

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