Toward the synthesis of macrolide aspergillide D

Kandimalla, Satheeshkumar Reddy; Reddy, B. V. Subba; Sabitha, Gowravaram

doi:10.1080/00397911.2019.1660900

Cited by 2 publications

(2 citation statements)

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“…Sabitha and co‐workers presented the linear synthesis of aspergillide D macrocycle core 581 involving the RCM reaction as a key step (Scheme 88). Aspergillide D is a 16‐membered marine macrolide, isolated from fungal strain Aspergillus sp [269] . Their synthetic journey began with the esterification of an alcohol 579 with acryloyl chloride in presence of TEA to produce a diene system 580 , an RCM precursor, which was then transformed into macrolactone 581 in 61% yield by means of ring closing metathesis in presence of G‐II catalyst.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

“…Aspergillide D is a 16-membered marine macrolide, isolated from fungal strain Aspergillussp. [269] Their synthetic journey began with the esterification of an alcohol 579 with acryloyl chloride in presence of TEA to produce a diene system 580, an RCM precursor, which was then transformed into macrolactone 581 in 61% yield by means of ring closing metathesis in presence of G-II catalyst. To complete the total synthesis of aspergillide D 582, macrolactone 581 was treated by TiCl 4 to cleave the acetonide group and benzyl ether, which remained unsuccessful.…”

Section: Studies Towards Fragment Syntheses Of Natural Products Based...mentioning

confidence: 99%

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Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Section: Studies Towards Fragment Syntheses Of Natural Products Based...mentioning

confidence: 99%