Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E

Reddy, D. Kumar; Shekhar, V.; Prabhakar, Pankaj; Babu, Dokuburra Chanti; Dasari, Ramesh; Siddhardha, Busi; Murthy, U. S. N.; Venkateswarlu, Y.

doi:10.1016/j.bmcl.2010.12.024

Cited by 16 publications

(7 citation statements)

References 16 publications

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“…The physical and spectroscopic data of 4 were in full agreement with the reported data. [ α ] D 25 = –37.1 ( c = 2.5, CHCl 3 ); ref . [ α ] D 25 = –36.7 ( c = 0.05, CHCl 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…(ii) Botryolide E ( 4 ) was isolated from cultures of fungicolous Botryotrichum sp . (NRRL 38180) and showed promising antibacterial activity against Bacillus subtilis (MTCC 441), Staphylococcus aureus (MTCC 96) and Escherichia coli (MTCC 443), as well as antifungal activity against Aspergillus niger (MTCC 1344) and Saccharomyces cerevisiae (MTCC 171) …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9‐epi‐Stagonolide C Employing Chiral Hexane‐1,2,3,5‐tetraol Derivatives as Building Blocks

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Kumar

2016

Eur J Org Chem

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An organocatalytic approach to the synthesis of (2R,3S)‐hexane‐1,2,3,5‐tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline‐catalyzed intermolecular aldol reaction between acetone and d‐glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.

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“…The physical and spectroscopic data of 4 were in full agreement with the reported data. [ α ] D 25 = –37.1 ( c = 2.5, CHCl 3 ); ref . [ α ] D 25 = –36.7 ( c = 0.05, CHCl 3 ).…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9‐epi‐Stagonolide C Employing Chiral Hexane‐1,2,3,5‐tetraol Derivatives as Building Blocks

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Kumar

2016

Eur J Org Chem

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“…layers were dried (Na 2 SO 4 ), concentrated, and purified by CC to obtain 15 (3.84 g, 86%). Spectroscopic data: see [9].…”

Section: Experimental Partmentioning

confidence: 99%

“…A reaction analogous to 10 ! 6 has been reported earlier using a different protecting group [9]. The OH group of 6 was protected as the PMB ether 16 by treatment with PMBCl and NaH.…”

mentioning

confidence: 99%

“…The latter was treated with the alkyne HCCCH 2 OPMB in the presence of BuLi and BF 3 · OEt 2 to furnish the homopropargyl alcohol 9. The free OH group of 9 was protected as TBDPS ether 14, and the PMB group of 14 was removed with DDQ to generate the propargyl alcohol 15 [9]. Subsequent reduction of 15 with Red-Al afforded the intermediate allylic alcohol 6 required for further steps.…”

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confidence: 99%

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Stereoselective Total Synthesis of Ophiocerin C through Two Different Approaches

Srilatha

Das

2014

Helvetica Chimica Acta

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ChemInform Abstract: Stereoselective First Total Synthesis, Confirmation of the Absolute Configuration and Bioevaluation of Botryolide‐E.

et al. 2011

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Stereoselective First Total Synthesis, Confirmation of the Absolute Configuration and Bioevaluation of Botryolide-E. -Botryolide-E (I) shows potent activity against S. aureus, good activity against E. coli and B. subtilis, as well as moderate to good antifungal activity. -(REDDY, D. K.; SHEKHAR, V.; PRABHAKAR, P.; BABU, D. C.; RAMESH, D.; SIDDHARDHA, B.; MURTHY, U. S. N.; VENKATESWARLU*, Y.; Bioorg. Med. Chem. Lett. 21 (2011) 3, 997-1000, http://dx.

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Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E

Cited by 16 publications

References 16 publications

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9‐epi‐Stagonolide C Employing Chiral Hexane‐1,2,3,5‐tetraol Derivatives as Building Blocks

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9‐epi‐Stagonolide C Employing Chiral Hexane‐1,2,3,5‐tetraol Derivatives as Building Blocks

Stereoselective Total Synthesis of Ophiocerin C through Two Different Approaches

ChemInform Abstract: Stereoselective First Total Synthesis, Confirmation of the Absolute Configuration and Bioevaluation of Botryolide‐E.

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