Enantioselective total syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H

Pandey, Rachana; Gehlawat, Anju; Prakash, Ranjana; Pandey, Satyendra Kumar

doi:10.1080/00397911.2018.1499037

Cited by 4 publications

(5 citation statements)

References 11 publications

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“…Recently, Kumar Pandey and co-workers described an efficient total syntheses of (-)-clavaminol A (1) and deacetyl (+)-clavaminol H (5) involving a Sharpless asymmetric dihydroxylation and a regioselective epoxide formation/opening followed by α-tosylation to install the chiral core structure. 53 As outlined in Scheme 15, α,β-unsaturated ester 77 was synthesized from commercially available n-decanol (76) by Swern oxidation followed by a Wittig reaction with (ethoxycarbonylmethylene)triphenylphosphorane. Sharpless asymmetric dihydroxylation 54 (1).…”

Section: Total Synthesis By Kumar Pandey and Colleagues (2018)mentioning

confidence: 99%

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Recent Advances in the Total Synthesis of Clavaminols

et al. 2018

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Clavaminols are a new class of long-chain 2-amino-3-alkanols that mostly contain 2R,3S-configurations. Owing to their interesting molecular architectures and promising activities, they have become popular targets for synthetic organic chemists. In this review, we highlight 12 total syntheses of clavaminols from different research groups during the period 2009 to 2018.1 Introduction2 Synthetic Approaches toward Clavaminols2.1 Total Synthesis by Chemla and Colleagues (2009)2.2 Total Synthesis by Greck and Colleagues (2010)2.3 Total Synthesis by Sutherland and Zaed (2011)2.4 Total Synthesis by Huang and Colleagues (2011)2.5 Total Synthesis by Kotora and Colleagues (2012)2.6 Total Synthesis by Kumar and Colleagues (2013)2.7 Total Synthesis by Prabhavathi Devi and Colleagues (2013 and 2016)2.8 Total Synthesis by Sarabia and Colleagues (2014)2.9 Total Synthesis by Mohapatra and Colleagues (2016)2.10 Total Synthesis by Lu and Colleagues (2016)2.11 Total Synthesis by Jin and Colleagues (2017)2.12 Total Synthesis by Kumar Pandey and Colleagues (2018)3 Conclusion

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Section: Total Synthesis By Kumar Pandey and Colleagues (2018)mentioning

confidence: 99%

“…Sharpless asymmetric dihydroxylation 54 (1). In this study, using a similar protocol, deacetyl (+)-clavaminol H (5) was also synthesized 53 from key intermediate 78.…”

Section: Total Synthesis By Kumar Pandey and Colleagues (2018)mentioning

confidence: 99%

Recent Advances in the Total Synthesis of Clavaminols

et al. 2018

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“…The typical chiral starting materials involve alanine,, , , , serine, Garner aldehyde, carbohydrates and glycidol . Asymmetric synthesis utilizes Sharpless epoxidation,, , Sharpless dihydroxylation, Henry reaction, azidirination, hydrazination via “enamine catalysis” and anti ‐aminohydroxylation , . Some of those syntheses afford only one stereoisomer of target 2‐aminoalkan‐2‐ol, but several exceptions can be found , , , .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

et al. 2020

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The simple preparation of the natural sphingoid bases possessing cytotoxic activity – the marine drugs Clavaminol A and Xestoaminol C and all their unnatural stereoisomers – in high enantiomeric purity (ca. 95 % of major enantiomer) was described. The individual enantiomers were obtained by the utilization of asymmetric Henry reaction. The diastereomers of target compounds were separated by column chromatography after transformation into corresponding 2‐phenyloxazoline derivatives. The individual stereoisomers of Clavaminol A and Xestoaminol C were evaluated for antiproliferative activity in cancer cell lines (A‐549; Jurkat; SH‐SY5Y, MG‐63). From the obtained IC50 values is obvious, that the stereoisomers of Xestoaminol C are more potent inhibitors of cell proliferation than the stereoisomers of Clavaminol A. Further, it was found, that stereoisomers with syn‐configuration exhibited larger antiproliferative effects in comparison with the stereoisomers having anti‐configuration, in both sphingoid bases. Nevertheless, the values of IC50 found for individual enantiomers in each of the enantiomeric pairs are rather comparable implying a possibility of using racemic mixtures for induction of cytotoxicity.

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“…Cyclization with Ph 3 C + BF 4 – /NaHCO 3 formed 54 in a 75% yield. TBAF removal of the silyl group yielded (±)-Clavaminol H − which could be converted into (±)-des-acetyl-Clavaminol H − upon heating with 6 M aqueous HCl solution. A similar strategy was applied for the synthesis of (±)- N -hexanoyldihydrosphingosine (Scheme B).…”

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confidence: 99%

Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine

et al. 2022

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We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine must be at least mildly activated, and a variety of such N-substituents are tolerated. The utility of this methodology is highlighted in facile preparations of the natural products (±)-Clavaminol H, (±)-dihydrosphingosine, and (±)-N-hexanoyldihydrosphingosine as well as a natural product analogue (±)-des-acetyl-Clavaminol H.

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Enantioselective total syntheses of (−)-clavaminol A and deacetyl (+)-clavaminol H

Cited by 4 publications

References 11 publications

Recent Advances in the Total Synthesis of Clavaminols

Recent Advances in the Total Synthesis of Clavaminols

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine

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