Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers

Dinda, Subal Kumar; Das, Sajal Kumar; Panda, Gautam

doi:10.1016/j.tet.2010.09.018

Cited by 22 publications

(11 citation statements)

References 26 publications

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“…According to Scheme 2, the azide group of 5 has been reduced to amine functionality by employing palladium on carbon (10% Pd/C) under hydrogen pressure in methanol at ambient temperature to yield the desired target compound 7 in 85% yield. [49,61] Biological evaluations. All the synthesized titled compounds 6a-6e and 7 were explored for in vitro bioactivities such as, antibacterial, antifungal, and cytotoxicity studies.…”

Section: Resultsmentioning

confidence: 99%

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Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Tangadanchu

Gundabathini

Bethala

et al. 2020

Journal of Heterocyclic Chem

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A new series of isomannide monoundecenoate-based 1,2,3-triazole analogs 6a-e were designed by employing click chemistry in good yields. in vitro bioactive assay manifested that the several target compounds exhibited promising antibacterial and antifungal activities. Notably, compounds having phenyl substituted triazole 6a, and hydroxy phenyl substituted triazole 6b possessed highly selective promising inhibition towards Gram-positive bacterial strains namely Bacillus subtilis and Staphylococcus aureus with MIC value of 3.9 μg/ mL. Further, these potential hybrids (6a and 6b) also exhibited highly impressive antifungal activity against the tested panel of Candida strains with MIC value of 3.9 μg/mL. Based on our in vitro preliminary antimicrobial study, these two compounds 6a and 6b have been identified as potential antimicrobial lead compounds. Moreover, all prepared derivatives were also evaluated for their in vitro cytotoxic activities against A549, MCF7, DU145 and HeLa cancer cell lines. The results indicated that only the hydroxy phenyl substituted triazole analog 6b displayed good cytotoxic activity towards all tested human cancer cell lines without any significant effects on normal cell line (HUVEC).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Tangadanchu

Gundabathini

Bethala

et al. 2020

Journal of Heterocyclic Chem

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“…Structurally, the 2-amino-3-alkanols isolated from Clavelina phlegraea were found to have (2R,3S)-configuration, which is opposite to that of the an antifungal agent (against Candida albicans with MIC 30 µg/mL) isolated from Clavelina oblonga and (2S,3R)-2-aminotetradecan-3-ol, an inhibitor of cell proliferation isolated from Spisula polynima. [14][15][16] Synthesis and complete biological profile of (2S,3R)-2-aminodecanols was well reported in literature. …”

Section: Introductionmentioning

confidence: 99%

General synthetic strategy for clavaminols A, C and H

Thirupathi¹,

Bharath²,

Mohapatra³

2015

Arkivoc

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Dedicated to Dr. J. S. Yadav on the occasion of his 65th birthday and in appreciation of his outstanding contributions to synthetic organic chemistry DOI: http://dx.doi.org/10.3998/ark.5550190.p009.281 Abstract A general and efficient synthetic strategy has been developed for the total syntheses of clavaminols A, C and H in 5 to 7 steps starting from (R)-Garners aldehyde following Grignard reaction, Corey-Bakshi-Shibata asymmetric reduction and selective acetylation as key steps with 42 to 59% overall yields, respectively.

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“…8−11 A common approach involves the preparation of the anti -vicinal amino-alcohol motif using starting materials from the chiral pool, such as carbohydrates and amino acids. In particular, several members of the sphingoid family of natural products have been synthesized by the stereoselective addition of nucleophiles to aldehydes derived from serine.…”

Section: Introductionmentioning

confidence: 99%

“…17 In our continuing studies of how the stereogenic centers within a molecule can influence the outcome of rearrangement reactions, we were interested in investigating the use of directed Overman rearrangements for the general preparation of sphingoid-type bases. We now report the synthesis of d - erythro -sphinganine ( 2 ) and the antitumor agent (+)-spisulosine ( 4 ) 7,11 using a MOM ether-directed Pd(II)-catalyzed Overman rearrangement to create the key anti -vicinal amino-alcohol moiety. We also describe a novel strategy for the preparation of d - ribo -phytosphingosine ( 3 ) and l - arabino -phytosphingosine ( 35 ) using an Overman rearrangement of a chiral allylic trichloroacetimidate.…”

Section: Introductionmentioning

confidence: 99%

Preparation of anti-Vicinal Amino Alcohols: Asymmetric Synthesis of d-erythro-Sphinganine, (+)-Spisulosine, and d-ribo-Phytosphingosine

2013

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Two variations of the Overman rearrangement have been developed for the highly selective synthesis of anti-vicinal amino alcohol natural products. A MOM ether-directed palladium(II)-catalyzed rearrangement of an allylic trichloroacetimidate was used as the key step for the preparation of the protein kinase C inhibitor d-erythro-sphinganine and the antitumor agent (+)-spisulosine, whereas the Overman rearrangement of chiral allylic trichloroacetimidates generated by the asymmetric reduction of an α,β-unsaturated methyl ketone allowed rapid access both to d-ribo-phytosphingosine and l-arabino-phytosphingosine.

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Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers

Cited by 22 publications

References 26 publications

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

Isomannide monoundecenoate‐based 1,2,3‐triazoles: Design, synthesis, and in vitro bioactive evaluation

General synthetic strategy for clavaminols A, C and H

Preparation of anti-Vicinal Amino Alcohols: Asymmetric Synthesis of d-erythro-Sphinganine, (+)-Spisulosine, and d-ribo-Phytosphingosine

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