Studies Towards the Stereoselective Total Synthesis of 7‐<i>O</i>‐methylnigrosporolide

Baikadi, Karunakar; Talakokkula, Anil; Narsaiah, A. Venkat

doi:10.1002/slct.201900863

Cited by 8 publications

(6 citation statements)

References 63 publications

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“…We therefore chose to use a key Ohira-Bestmann homologation, similar to Narsaiah's strategy, but with slight modification to shorten the synthetic sequence and to give a higher enantiopurity of the intermediate. Ring opening of commercially available (S)-propylene oxide (7) by allylmagnesium bromide in the presence of catalytic CuI furnished the corresponding chiral alcohol, which was protected with a TBS group to give the TBS ether 8 in 90% yield. 8 Hydroboration with BH 3 •SMe 2 in THF led, after oxidative workup, to the formation of chiral alcohol 9 in 78% yield and 96% ee (determined by chiral HPLC).…”

Section: Cluster Synlettmentioning

confidence: 99%

“…Here, we report a convergent total synthesis of 7-O-methylnigrosporolide (1) and pestalotioprolide D (2), as well as an evaluation of their cytotoxic activities against six human cancer cell lines. In 2019, Narsaiah et al reported the studies toward a stereoselective total synthesis of 1, 7 which our research group had already pursued with similar key synthetic strategies. Their key synthetic features involved acetylide addition and macrolactonization starting from D-mannitol and hex-5-en-1-ol; however, their synthesis suffered from an unsuccessful final removal of a MOM protecting group on the C4-hydroxy group to give the natural product.…”

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confidence: 99%

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Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D

Thiraporn

Iawsipo

Tadpetch

2022

Synlett

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A convergent total synthesis of 7-O-methylnigrosporolide and pestalotioprolide D has been accomplished in 17 longest linear steps starting with 1.7% and 2.6% overall yields, respectively, starting from (S)-propylene oxide and known (S)-benzyl glycidyl ether. Our synthesis exploited acetylide addition and Shiina macrolactonization to assemble the macrocycle, Lindlar reduction, Wittig and Still–Gennari olefination to construct the three olefins as well as a Jacobsen hydrolytic kinetic resolution to install the stereogenic center. The selection of silyl protecting group of C-4 alcohol was crucial for final deprotection step. Our synthesis also led to a hypothesis that pestalotioprolide D could be an artifact of 7-O-methylnigrosporolide. Cytotoxic activity of both synthetic compounds against six human cancer cell lines was evaluated. Synthetic pestalotioprolide D showed more potent cytotoxic activity against all cancer cell lines tested than 7-O-methylnigrosporolide, and the SiHa cervical cancer cell line was the most sensitive cell to both synthetic compounds.

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Section: Cluster Synlettmentioning

confidence: 99%

mentioning

confidence: 99%

Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D

Thiraporn

Iawsipo

Tadpetch

2022

Synlett

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“…[35] A 13 step total synthesis method has been reported for the preparation of 27 with the starting material D-mannitol and 5-hexenol leading to 10.5 % w/w yield (Table 1; Figure 9). [65]…”

Section: Macrolidesmentioning

confidence: 99%

Exploration of Potent Cytotoxic Molecules from Fungi in Recent Past to Discover Plausible Anticancer Scaffolds

Shevkar

Pradhan

Armarkar

et al. 2022

Chemistry & Biodiversity

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Fungi are known to produce diverse scaffolds possessing unique biological activities, however, to date, no molecule discovered from a fungal source has reached the market as an anti‐cancer drug. Every year number of cytotoxic molecules of fungal origin are getting published and critical analysis of those compounds is necessary to identify the potent ones. A review mentioning the best cytotoxic fungal metabolites and their status in the drug development was published in 2014. In this report, we have included 176 cytotoxic molecules isolated from fungi after 2014 and categorized them according to their potencies such as IC50 values below 1 μM, 1–5 μM, and 5–10 μM. The emphasis was given to those 42 molecules which have shown IC50 less than 1 μM and discussed to a great extent. This review shall provide potent scaffolds of fungal origin which can be given priority in the development as a drug candidate for cancer therapeutics.

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“…[168] Recently, a wide range of 14-membered bioactive naturally occurring compounds were extracted from mangrove derived endophytic fungus Pestolotiopsis microspora by Liu and coworkers. [169] Those are 7 new macrolides pestalotioprolides CÀ H, and 7-O-methylnigrosporolide. Among them, 7-O-meth- ylnigrosporolide contain structural aspects and noticeable biological significance.…”

Section: -Membered Macrolidesmentioning

confidence: 99%

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

et al. 2020

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The Wittig reaction involves the synthesis of an alkene via the conversion of an aldehyde or ketone with the already generated ylide from a phosphonium salt. Significantly, when this important name reaction is employed the desired alkenes are constructed via a predictable manner, thus resultant particularly are useful in the total synthesis of natural products and synthetic complex organic compounds with definite geometric isomers, exhibiting diverse biological potencies. In this review we try to highlight the applications of the Wittig reaction as an efficient and attractive strategy in the total synthesis of macrolides from 2008 to 2020.

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Studies Towards the Stereoselective Total Synthesis of 7‐O‐methylnigrosporolide

Cited by 8 publications

References 63 publications

Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D

Total Synthesis and Cytotoxic Activity of 7-O-Methylnigrosporolide and Pestalotioprolide D

Exploration of Potent Cytotoxic Molecules from Fungi in Recent Past to Discover Plausible Anticancer Scaffolds

Applications of Wittig Reaction in the Total Synthesis of Natural Macrolides

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