Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines

Swapan Majumdar; Jewel Hossain; Ramalingam Natarajan; Ashish K. Banerjee; Dilip K. Maiti

doi:10.1039/C5RA22436E

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Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines†

Swapan Majumdar,*^a Jewel Hossain,^a Ramalingam Natarajan,^b Ashish K. Banerjee^b and Dilip K. Maiti*^c

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^a Department of Chemistry, Tripura University, Suryamaninagar 799 022, India
E-mail: smajumdar@tripurauniv.in
Fax: +91-381-2374802
Tel: +91-381-237-9070

^b Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700 032, India

^c Department of Chemistry, University of Calcutta, 92 A. P. C. Raod, Kolkata-700009, India
E-mail: dkmchem@caluniv.ac.in
Fax: +91-33-2351-9755
Tel: +91-33-2350-9937

Abstract

The highly selective synthesis of phthalate templated bridged isoxazoline macrocyclic lactones is demonstrated using readily accessible carbohydrate precursors via intramolecular nitrile oxide–alkene cycloaddition. The structures of the macrocycles were established by 2D NMR as well as X-ray diffraction study. The orientation of the bridged isoxazoline ring is dependent on the distance between the 1,3-dipole and dipolarophile. The macrocycles are amenable to further transformations to higher amino sugars by sequential removal of the phthalate template and reductive cleavage of the isoxazoline moiety.

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DOI: https://doi.org/10.1039/C5RA22436E
Article type: Communication
Submitted: 26 Oct 2015
Accepted: 01 Dec 2015
First published: 03 Dec 2015

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RSC Adv., 2015,5, 106289-106293

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Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines

S. Majumdar, J. Hossain, R. Natarajan, A. K. Banerjee and D. K. Maiti, RSC Adv., 2015, 5, 106289 DOI: 10.1039/C5RA22436E

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Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines†

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Phthalate tethered strategy: carbohydrate nitrile oxide cycloaddition to 12–15 member chiral macrocycles with alkenyl chain length controlled orientation of bridged isoxazolines

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