@article { ISI:000230044900021, title = {[6+3] cycloaddition of fulvenes with 3-oxidopyrylium betaine: a novel methodology for the synthesis of fused cyclooctanoid natural products}, journal = {Tetrahedron Letters}, volume = {46}, number = {28}, year = {2005}, month = {JUL}, pages = {4785-4788}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Fulvenes undergo an easy [6+3] cycloaddition with 3-oxidopyrylium betaines leading to 5-8 fused oxabridged cyclooetanoids. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {cyclooctanoids, fulvenes, oxidopyrylium betaines, [6+3] cycloaddition}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2005.05.042}, author = {Radhakrishnan, K. V. and Krishnan, K. Syam and Bhadbhade, Mohan M. and Bhosekar, Gaurav V.} } @article { ISI:000228147400027, title = {First enantiospecific synthesis of (+)-beta-herbertenol}, journal = {Tetrahedron}, volume = {61}, number = {15}, year = {2005}, month = {APR}, pages = {3873-3879}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

The first enantiospecific synthesis of (+)-beta-herbertenol, from naturally occurring R-(+)-citronellal, employing Taber{\textquoteright}s diazo decomposition protocol as the key step, is described. (c) 2005 Elsevier Ltd. All rights reserved.

}, keywords = {citronellal, diazo decomposition, enantiospecific}, issn = {0040-4020}, doi = {10.1016/j.tet.2005.01.050}, author = {Chavan, Subhash P. and Thakkar, M. and Kharul, Rajendra K. and Pathak, A. B. and Bhosekar, Gaurav V. and Bhadbhade, Mohan M.} } @article { ISI:000231767400051, title = {Identical molecular strings woven differently by intermolecular interactions in dimorphs of myo-inositol 1,3,5-orthobenzoate}, journal = {Crystal Growth \& Design}, volume = {5}, number = {5}, year = {2005}, month = {SEP}, pages = {1977-1982}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

myo-Inositol 1,3,5-orthobenzoate exhibits polymorphic behavior depending upon the solvent and time allowed for crystallization. Long plates (form I, monoclinic P2(1)/n) are produced on crystallization from methanol, while crystallization from ethyl acetate mostly yielded squarish plates (form II, monoclinic P2(1)/c). The latter could also be obtained by achieving rapid nucleation from a supersaturated solution of methanol. Remarkably, the overall conformation of the individual molecules is very similar in both polymorphs, although free rotations were possible for the phenyl ring and for the three O-H groups. O-H center dot center dot center dot O linked one-dimensional isostructural molecular strings in the two forms weave differently by weak intermolecular interactions to produce the dimorphs. Striking difference is seen in the {\textquoteleft}{\textquoteleft}zipping{\textquoteright}{\textquoteright} of molecular layers via phenyl center dot center dot center dot phenyl contacts; thermodynamic crystals of form I utilize a well-recognized {\textquoteleft}{\textquoteleft}edge-to-face{\textquoteright}{\textquoteright} herringbone pattern, making C-H center dot center dot center dot pi interactions, whereas the kinetic crystals of form II show rather uncommon {\textquoteleft}{\textquoteleft}edge-to-edge{\textquoteright}{\textquoteright} organization, which makes short Ph-H center dot center dot center dot H-Ph contacts.

}, issn = {1528-7483}, doi = {10.1021/cg050272j}, author = {Bhosekar, Gaurav V. and Murali, Chebrolu and Gonnade, Rajesh G. and Shashidhar, M. S. and Bhadbhade, Mohan M.} } @article { ISI:000232405500048, title = {Synthesis and intramolecular nitrile oxide cycloaddition of 3,5 {\textquoteleft}-ether-linked pseudooligosaccharide derivatives: an approach to chiral macrooxacycles}, journal = {Journal of Organic Chemistry}, volume = {70}, number = {21}, year = {2005}, month = {OCT}, pages = {8579-8582}, publisher = {AMER CHEMICAL SOC}, type = {Article}, address = {1155 16TH ST, NW, WASHINGTON, DC 20036 USA}, abstract = {

[GRAPHIC] 3,5{\textquoteright}-Ether-linked pseudooligopentose derivatives were synthesized for the first time from readily available carbohydrate precursors. The 1,2-isopropylidene-protected ether-linked oligopentoses are potentially important as precursors of novel RNA analogues. Intramolecular cycloaddition of the nitrile oxides prepared from these derivatives led to the diastereoselective formation of chiral isoxazolines fused to 10-16-membered oxacycles. The stereochemistry of some of these isoxazolines was established by X-ray diffraction and NOESY analysis.

}, issn = {0022-3263}, doi = {10.1021/jo050689w}, author = {Sengupta, J. and Mukhopadhyay, R. and Bhattacharjya, A. and Bhadbhade, Mohan M. and Bhosekar, Gaurav V.} } @article { ISI:000238171600014, title = {[6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaine: a novel methodology toward the synthesis of 5-8 fused oxabridged cyclooctanoids}, journal = {Tetrahedron}, volume = {62}, number = {25}, year = {2006}, month = {JUN}, pages = {5952-5961}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, type = {Article}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

Pentafulvenes undergo a facile [6+3] cycloaddition with 3-oxidopyrylium betaine, generated from the corresponding pyranulose acetate, leading to the formation of 5-8 fused oxabridged cyclooctanoids. The product is formed by a [6+3] cycloaddition, followed by a 1,5-hydrogen shift of the initially formed [6+3] adduct. The reaction was found to be general and a number of fulvenes with a wide range of substituents at the exocyclic double bond, that is, at the C6 position followed a similar reactivity pattern. The [6+3] adduct, a 5-8 fused oxabridged cyclooctanoid, is potentially amenable to a number of synthetic transformations due to the presence of an alpha, beta-unsaturated ketone and cyclopentadiene part. By selecting appropriately substituted fulvene and pyranulose acetates, it is possible to use this methodology for the synthesis of a wide range of 5-8 fused cyclooctanoids. The experimental results have been rationalized on the basis of theoretical calculations. (c) 2006 Elsevier Ltd. All rights reserved.

}, keywords = {fulvenes, oxabridged cyclooctanoids, oxidopyrylium betaine, [6+3] cycloaddition}, issn = {0040-4020}, doi = {10.1016/j.tet.2006.04.017}, author = {Krishnan, K. Syam and Sajisha, V. S. and Anas, S. and Suresh, C. H. and Bhadbhade, Mohan M. and Bhosekar, Gaurav V. and Radhakrishnan, K. V.} }