Studies toward the Total Synthesis of Carolacton

Sabitha, Gowravaram; Shankaraiah, K.; Prasad, M. Nagendra; Yadav, J. S.

doi:10.1055/s-0032-1317700

Cited by 14 publications

(8 citation statements)

References 9 publications

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“…12,13 There have also been a handful of publications toward the synthesis of carolacton that fit outside the scope of this account. [14][15][16][17] To complete our route toward the natural product, we proposed precursor acid 2 and side-chain 3 (Scheme 1). 11 Starting from gulonolactone-derived diol 4, oxidation and subsequent Wittig olefination allows for synthesis of alkene 5 (Scheme 2).…”

Section: Back To the Beginning: The Initial Synthetic Highlightsmentioning

confidence: 99%

Collaboration in Natural Product Total Synthesis: Carolacton – A Decade of Discovery

Solinski

Wuest

2020

Synlett

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Carolacton, a macrocyclic natural product with impressive anti-biofilm biological activity, has been a focus in multiple research groups for the past decade. Chemists and biologists, alike, have been interested in uncovering the mechanism of action and have made great strides towards this goal. Carolacton causes cellular defects in Streptococcus mutans biofilm, which leads to decreases in cellular viability. As biological targets have been uncovered, synthetic chemists have devised synthetic routes that have helped uncover the important chemical functionalities that lead to biological activity. Herein, we discuss our synthetic collaboration that galvanized an entire research program around the natural product carolacton.

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Section: Back To the Beginning: The Initial Synthetic Highlightsmentioning

confidence: 99%

Collaboration in Natural Product Total Synthesis: Carolacton – A Decade of Discovery

Solinski

Wuest

2020

Synlett

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“…In addition to the total syntheses discussed above, carolacton has been the subject of significant synthetic effort, resulting in a number of partial syntheses and one formal synthesis (Scheme ). In 2013, Ghosh reported routes to the alcohol ( 131 ) and alkyne ( 133 ) .…”

Section: Other Examples Of 12‐membered Macrolactonesmentioning

confidence: 99%

“…In 2013, Reddy published a route to the carolacton macrocycle 142 via an esterification/deprotection/RCM sequence (Scheme C). In the same year, Sabitha reported the successful synthesis of the full carolacton carbon skeleton 145 , also utilizing an NHK coupling of 143 and 144 in a manner similar to Kirschning (Scheme D). Continuing their work toward carolacton, Reddy recently published a route to the C1‐C16 fragment 137 , beginning with the Roche ester 134 and procuring the precursor for an esterification/RCM which would provide carolacton (Scheme B).…”

Section: Other Examples Of 12‐membered Macrolactonesmentioning

confidence: 99%

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Twelve‐membered macrolactones: privileged scaffolds for the development of new therapeutics

Brzozowski

Wuest

2017

Chem Biol Drug Des

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Natural products commonly produced as secondary metabolites of various plants and micro-organisms represent a diverse chemical space of compounds. The diversity of natural products makes them an attractive target for interrogation by both chemists and biologists alike. Indeed, the study of 12-membered macrolactones has already led to the discovery of lead drug compounds and new biological targets, which has motivated the development of diverted total synthetic routes to libraries of analogs. This review explores the discovery, biological characterization, and synthesis of several 12-membered macrolactones, exploiting examples that underscore their importance in the drug discovery field. It is our hope that this review will motivate further interest in this class of natural products, a group of molecules that we think merit the classification of 'privileged scaffolds' within the medicinal chemistry community, to further investigate and develop novel compounds with promising bioactivity. K E Y W O R D Santibiotic, biosynthesis, diverted total synthesis, macrolactone, natural product

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“…Sabitha et al 5 described the synthesis of the C1-C19 segment of carolacton, starting from (À)-b-citronell, D-ribose and a homopropargylic alcohol, and by using Nozaki-Hiyama-Kishi (NHK) coupling, cross-metathesis and Evans aldol reactions.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of the macrocyclic core (C7–C19) of carolacton

Sharma

Reddy

2013

RSC Adv.

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Carolacton, a secondary metabolite, was isolated from the myxobacterium Sorangium cellulosum. It exhibits excellent antibacterial activity at nanomolar concentrations. We report the synthesis of the macrocyclic core of carolacton, comprising the C7-C19 fragment with five out of the eight stereocentres. The key reactions involved are: Sharpless asymmetric epoxidation, metal chelated epoxide opening, Yamaguchi esterification and ring closing metathesis (RCM). The present study utilizes a simple synthetic strategy, adopting asymmetric and chiron approaches.

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Studies toward the Total Synthesis of Carolacton

Abstract: An efficient synthesis of the C1-C19 segment of carolacton is described, starting from D-ribose, (-)-β-citronellene and a homopropargylic alcohol, and which employs a Nozaki-HiyamaKishi (NHK) coupling as the key step. Other important steps are cross-metathesis and Evans aldol reactions.

Cited by 14 publications

References 9 publications

Collaboration in Natural Product Total Synthesis: Carolacton – A Decade of Discovery

Collaboration in Natural Product Total Synthesis: Carolacton – A Decade of Discovery

Twelve‐membered macrolactones: privileged scaffolds for the development of new therapeutics

Stereoselective synthesis of the macrocyclic core (C7–C19) of carolacton

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