Studies towards the Synthesis of Aldgamycin – M

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

doi:10.1002/slct.201803591

Cited by 8 publications

(8 citation statements)

References 29 publications

(10 reference statements)

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“…The successful conquest of aldgamycin N ( 2 ) [9,11] as well as the bare macrolide mycinolide IV ( 3 ), [8] which itself had been a prominent target in the past, [12–15] can be taken as proof‐of‐concept. It relied on the use of compound 5 as the common starting point en route to both product subsets, for which a practical synthesis viable on decagram scale could be established [8] .…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

Späth

Fürstner

2022

Chemistry A European J

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The total synthesis of the 16‐membered macrolide mycinamicin IV is outlined, which complements our previously disclosed, largely catalysis‐based route to the aglycone. This work must also be seen in the context of our recent conquest of aldgamycin N, a related antibiotic featuring a similar core but a distinctly different functionalization pattern. Taken together, these projects prove that the underlying blueprint is integrative and hence qualifies for a collective approach to this prominent class of natural products. In both cases, the final glycosylation phase mandated close attention and was accomplished only after robust de novo syntheses of the (di)deoxy sugars of the desosamine, chalcose, mycinose and aldgarose types had been established. Systematic screening of the glycosidation promoter was also critically important for success.

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Section: Methodsmentioning

confidence: 99%

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

Späth

Fürstner

2022

Chemistry A European J

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“…Muralikrishna et al [88] . formed the macrolide core out of homo allyl alcohol fragment 78.6 and the acid C(1)−C(12) fragment 78.3 being made out of meso‐diol, which was converted to aldehyde 78.1 .…”

Section: Thiazolidinethione Chiral Auxiliaries In Asymmetric Synthesismentioning

confidence: 99%

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

2021

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Nature is incessantly affianced to construct bioactive and structurally intriguing compounds with magnificent three‐dimensional frameworks in the Universe. The inadequacy of these naturally occurring precious compounds prompted several minds of chemists to synthesise them in a laboratory for a thorough evaluation of their medicinal and clinical properties via a structure‐activity relationship study. Finding an optimised methodology to synthesise chiral natural products has always been challenging in synthetic organic chemistry, particularly the formation of asymmetric carbon‐carbon bonds adhering to the existing stereochemistry. In this context, chiral auxiliaries have proven to be effective tools for inducing chirality during the synthesis of chiral molecules. In fact, the chiral auxiliary will allow us to control the synthesis of many enantiomerically pure isomers in natural product synthesis. In this area, the significant contribution of the Evans’ chiral auxiliary in TiCl4‐mediated asymmetric aldol reactions to the installation of known configurations in organic synthetic chemistry motivated us to compile an exhaustive and systematic summary of the relevant research findings published in the last two decades.

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“…Over this enticing outlook, however, one must not forget the lessons learnt from previous studies in this field. Members of the mycinamicin family were targeted in the past [15–19] . This precedent shows the delicacy of these compounds and illustrates the numerous challenges to be met en route to this sensitive chemotype.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Mycinolide IV and Path‐Scouting for Aldgamycin N

et al. 2021

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Proof‐of‐concept is provided that a large estate of 16‐membered macrolide antibiotics can be reached by a “unified” approach. The key building block was formed on scale by an asymmetric vinylogous Mukaiyama aldol reaction; its alkene terminus was then converted either into the corresponding methyl ketone by Wacker oxidation or into a chain‐extended aldehyde by catalyst‐controlled branch‐selective asymmetric hydroformylation. These transformations ultimately opened access to two structurally distinct series of macrolide targets. Notable late‐stage maneuvers comprise a rare example of a ruthenium‐catalyzed redox isomerization of an 1,3‐enyne‐5‐ol into a 1,3‐diene‐5‐one derivative, as well as the elaboration of a tertiary propargylic alcohol into an acyloin by trans‐hydrostannation/Chan‐Lam‐type coupling. Moreover, this case study illustrates the underutilized possibility of forging complex macrolactone rings by transesterification under essentially neutral conditions.

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Studies towards the Synthesis of Aldgamycin – M

Cited by 8 publications

References 29 publications

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Total Synthesis of Mycinolide IV and Path‐Scouting for Aldgamycin N

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Studies towards the Synthesis of Aldgamycin – M

Cited by 8 publications

References 29 publications

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics

TiCl4‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis

Total Synthesis of Mycinolide IV and Path‐Scouting for Aldgamycin N

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Product

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TiCl₄‐Promoted Asymmetric Aldol Reaction of Oxazolidinones and its Sulphur‐Congeners for Natural Product Synthesis