Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3 |
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| Authors: | Elias A. Couladouros Vassilios I. Moutsos |
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| Affiliation: | a Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, GR 118 55 Athens, Greece
b Natural Product Synthesis and Bioorganic Chemistry Laboratory, Institute of Physical Chemistry, NCSR ‘Demokritos’, PO Box 60228, GR 153 10 Ag. Paraskevi, Greece |
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| Abstract: | A synthetic strategy, based on intramolecular addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine, towards the naturally occurring marine toxins oxazinin-1, -2 and -3 is presented. The expedient first total synthesis of oxazinin-3, thus accomplished, demonstrated the efficiency of the approach and established the absolute stereochemistry of oxazinin-3 as 2S,5S. |
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| Keywords: | Total synthesis Oxazinins Morpholinone 3-Methyleneindolenine |
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