Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III

Gurjar, Mukund K.; Nagaprasad, Ravi; Ramana, Chepuri V.; Karmakar, Sukhen; Mohapatra, Debendra K.

doi:10.3998/ark.5550190.0006.326

Cited by 20 publications

(2 citation statements)

References 13 publications

(20 reference statements)

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“…When using Grubbs II catalyst, the reaction proceeded faster than with Grubbs I catalyst (6 h vs. 24 h), for comparable observations see ref. [ 12 , 16 , 17 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis by Ring Closing Metathesis and Cytotoxic Evaluation of Novel Thienylmacrolactones

Krauß

Köbler²,

Miller³

et al. 2012

Sci. Pharm.

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This paper describes the synthesis and biological evaluation of macrolactones containing a thienyl substituent as simple analogues of epothilones. The compounds were prepared in a brief and efficient manner from thiophene-2-carbaldehyde using a ring-closing metathesis with Grubbs I or Grubbs II catalyst as the key step. The target lactones showed only insignificant cytotoxicity, while an intermediate simple thienyl carbinol showed very promising cytotoxicity.

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“…When using Grubbs II catalyst, the reaction proceeded faster than with Grubbs I catalyst (6 h vs. 24 h), for comparable observations see ref. [ 12 , 16 , 17 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis by Ring Closing Metathesis and Cytotoxic Evaluation of Novel Thienylmacrolactones

Krauß

Köbler²,

Miller³

et al. 2012

Sci. Pharm.

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“…The first total synthesis of 1 was published by us in 2002 . In subsequent years, syntheses of either the natural product or its non-natural enantiomer were reported in the literature by up to six groups . No nominal synthesis of 2 has been published so far (see below, however).…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Total Synthesis and Absolute Configuration of the Natural Decanolides (−)-Microcarpalide and (+)-Lethaloxin. Identity of (+)-Lethaloxin and (+)-Pinolidoxin

et al. 2005

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[reaction: see text] Convergent, stereoselective syntheses of the pharmacologically active, naturally occurring lactones (-)-microcarpalide and (+)-lethaloxin have been achieved from the commercially available, chiral reagents (R)-glycidol, (S,S)-tartaric acid, and d-ribose as the starting materials. These syntheses have further served to establish the hitherto unknown absolute configuration of (+)-lethaloxin and to show its identity with (+)-pinolidoxin.

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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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Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III

Abstract: Total synthesis of naturally occurring microcarpalide and herbarumin III are described. The ringclosing metathesis (RCM) approach to coin the medium sized rings present in their molecular structures form the basic premise of this investigation.

Cited by 20 publications

References 13 publications

Synthesis by Ring Closing Metathesis and Cytotoxic Evaluation of Novel Thienylmacrolactones

Synthesis by Ring Closing Metathesis and Cytotoxic Evaluation of Novel Thienylmacrolactones

Stereoselective Total Synthesis and Absolute Configuration of the Natural Decanolides (−)-Microcarpalide and (+)-Lethaloxin. Identity of (+)-Lethaloxin and (+)-Pinolidoxin

Olefin Ring‐Closing Metathesis

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