Total Synthesis of Sacrolide A by Following a Nozaki‐Hiyama‐Kishi Macrocyclization Strategy

Jena, Bighnanshu K.; Reddy, Aedula Vishnu V.; Mohapatra, Debendra K.

doi:10.1002/ajoc.201500537

Cited by 7 publications

(4 citation statements)

References 28 publications

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“…[144] The bioactive natural product sacrolide A (102) comprises two chiral centers, a cis-configured double bond in the side chain, and a vinylic ketone. [145] In 2016, the stereoselective total synthesis of oxylipin macrolide (+)-sacrolide A (102) was accomplished by Mohapatra et al through Yamaguchi method. [145] The macrolactone core was built via acid fragment (97) and alcohol fragment (99).…”

Section: Total Synthesis Of Sacrolide Amentioning

confidence: 99%

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Applications of Yamaguchi Method to Esterification and Macrolactonization in Total Synthesis of Bioactive Natural Products

Majhi

2021

ChemistrySelect

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Yamaguchi protocol provides functionalized esters regioselectively from carboxylic acids and alcohols employing 2,4,6trichlorobenzoyl chloride as the condensation reagent in the presence of a stoichiometric amount of 4-N,N-dimethylaminopyridine. The key features of this method comprise a high yield of esters, short reaction time, mild conditions, macrocyclic lactone ring formation, and regioselective preparation of highly functionalized esters. Such beneficial quality of this method as a whole have motivated the organic chemist and biological community to explore the application of Yamaguchi protocol in more heights and as a result, the present overview is aimed to cover the application of this method as a key step in the area of the total synthesis of bioactive natural products. The present review tries to focus on the natural sources, structures, and biological activities of the promising natural products elegantly.

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Section: Total Synthesis Of Sacrolide Amentioning

confidence: 99%

“…[145] In 2016, the stereoselective total synthesis of oxylipin macrolide (+)-sacrolide A (102) was accomplished by Mohapatra et al through Yamaguchi method. [145] The macrolactone core was built via acid fragment (97) and alcohol fragment (99). The acid fragment (97) was obtained from 1,9-Scheme 21.…”

Section: Total Synthesis Of Sacrolide Amentioning

confidence: 99%

Applications of Yamaguchi Method to Esterification and Macrolactonization in Total Synthesis of Bioactive Natural Products

Majhi

2021

ChemistrySelect

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“…The example of telithromycin shows that in some cases the facial selectivity of the organochromium addition is not vital, because the generated alcohol in the NHTK reaction should be oxidized to afford the natural product. This kind of methodology (NHTK cyclyzation and oxidation) is used in many total syntheses, such as that of narbonolide, , 5-( Z )-7-oxozeaenol and its analogs, (−)-atrop-abyssomicin C, , and sacrolide A (Figure ).…”

Section: Uses Of the Nhtk Reaction In Total Synthesismentioning

confidence: 99%

Role of the Nozaki–Hiyama–Takai–Kishi Reaction in the Synthesis of Natural Products

2017

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The Nozaki-Hiyama-Takai-Kishi (NHTK) reaction was discovered in the late 1970s and, since then, its main application has been its use in total synthesis. In this comprehensive review, the efficiency of the NHKT reaction in the synthesis of a great number of different scaffolds present in complex natural products is analyzed. The preparation of enol and allylic and propargylic alcohol motifs is discussed, highlighting factors such as yield, chemoselectivity, stereoselectivity, or the importance of protecting groups. The review is divided into two main sections: intermolecular and intramolecular NHTK reactions. A final discussion about the current "state-of-art" and future perspectives for the use of this transformation in total synthesis is also included.

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“…Sacrolide A embedded with a 14‐membered macrolide, an α , β ‐unsaturated ketone, and a cis‐ configured double bond with a side chain including two chiral centers (Figure ). Interesting structural features and promising biological properties of sacrolide A have attracted us and other groups to undertake its total synthesis . In this context, we wish to disclose a simple and straightforward strategy for the synthesis of sacrolide A in an efficient manner.…”

Section: Introductionmentioning

confidence: 99%