Synthesis of isomeric corniculatolides

Gajanan N. Raut; Kasturi Chakraborty; Priyanka Verma; Rajesh S. Gokhale; D. Srinivasa Reddy

doi:10.1016/j.tetlet.2012.09.010

Synthesis of isomeric corniculatolides

Gajanan N. Raut, Kasturi Chakraborty, Priyanka Verma, Rajesh S. Gokhale, D. Srinivasa Reddy

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7 Scopus citations

Abstract

Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H ₃₇Rv) and found no significant inhibitory activity at 100 μg/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work.

Original language	English
Pages (from-to)	6343-6346
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2012.09.010
State	Published - Nov 21 2012

Keywords

Diaryl ether
Isocorniculatolide
Macrocyclization
Mitsunobu reaction
Total synthesis

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10.1016/j.tetlet.2012.09.010

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@article{d59f515ffe2246398bf3fad8c6a7b6bd,

title = "Synthesis of isomeric corniculatolides",

abstract = "Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H 37Rv) and found no significant inhibitory activity at 100 μg/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work.",

keywords = "Diaryl ether, Isocorniculatolide, Macrocyclization, Mitsunobu reaction, Total synthesis",

author = "Raut, {Gajanan N.} and Kasturi Chakraborty and Priyanka Verma and Gokhale, {Rajesh S.} and {Srinivasa Reddy}, D.",

note = "Funding Information: Financial support from NCL , Pune (Start-up Grant, MLP022126 ) and CSIR, New Delhi (NCL-IGIB joint research collaboration program, NWP0013) is gratefully acknowledged. G.N.R. thanks CSIR, New Delhi, for the award of junior research fellowship. We thank the reviewer of this manuscript for useful suggestions. ",

year = "2012",

month = nov,

day = "21",

doi = "10.1016/j.tetlet.2012.09.010",

language = "English",

volume = "53",

pages = "6343--6346",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "47",

}

TY - JOUR

T1 - Synthesis of isomeric corniculatolides

AU - Raut, Gajanan N.

AU - Chakraborty, Kasturi

AU - Verma, Priyanka

AU - Gokhale, Rajesh S.

AU - Srinivasa Reddy, D.

N1 - Funding Information: Financial support from NCL , Pune (Start-up Grant, MLP022126 ) and CSIR, New Delhi (NCL-IGIB joint research collaboration program, NWP0013) is gratefully acknowledged. G.N.R. thanks CSIR, New Delhi, for the award of junior research fellowship. We thank the reviewer of this manuscript for useful suggestions.

PY - 2012/11/21

Y1 - 2012/11/21

N2 - Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H 37Rv) and found no significant inhibitory activity at 100 μg/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work.

AB - Synthesis of three natural macrolides 11-O-methylcorniculatolide A, 11-O-methylisocorniculatolide A and isocorniculatolide A is reported using a simple, straight forward and high-yielding route. The present synthesis confirms the assigned molecular structures and provides an access to sufficient quantities of the natural products for the biological evaluation. In addition, we have determined the anti-TB potential of the three natural compounds using Alamar-Blue assay (H 37Rv) and found no significant inhibitory activity at 100 μg/ml. Excellent yields, short sequence and useful SAR information are the highlights of the present work.

KW - Diaryl ether

KW - Isocorniculatolide

KW - Macrocyclization

KW - Mitsunobu reaction

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84867871888&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.09.010

DO - 10.1016/j.tetlet.2012.09.010

M3 - Article

AN - SCOPUS:84867871888

SN - 0040-4039

VL - 53

SP - 6343

EP - 6346

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Synthesis of isomeric corniculatolides

Abstract

Keywords

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