Abstract
The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran- 2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2- enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
Keywords: Lactone intermediates, Wittig olefination, maruoka asymmetric allylation, 6 -(R)-4-oxopent-2-enyl 5, 6-dihydro- 2H-pyran-2-one, (R)- rugulactone, enantiomer.
Letters in Organic Chemistry
Title:Simple Stereoselective Synthesis of Unsaturated Lactone Intermediates and Their Conversion into Natural Dihydropyranones and Their Enantiomers#
Volume: 10 Issue: 5
Author(s): Digambar Balaji Shinde, Boddu Shashi Kanth, Avula Satyakumar, V.T. Kamble and Biswanath Das
Affiliation:
Keywords: Lactone intermediates, Wittig olefination, maruoka asymmetric allylation, 6 -(R)-4-oxopent-2-enyl 5, 6-dihydro- 2H-pyran-2-one, (R)- rugulactone, enantiomer.
Abstract: The stereoselective synthesis of the unsaturated lactone intermediates, (S) - and (R)-2-(6-oxo-3, 6-dihydro-2Hpyran- 2-yl) acetaldehydes has been accomplished from propane 1,3 diol employing Maruoka asymmetric allylation and ring closing metathesis reaction. The intermediates were converted into two natural dihydropyranones, 6 (R)-4-oxopent-2- enyl 5,6-dihydro-2H-pyran-2-one and (R)- rugulactone and their enantiomers through Wittig olefination.
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Cite this article as:
Shinde Digambar Balaji, Kanth Boddu Shashi, Satyakumar Avula, Kamble V.T. and Das Biswanath, Simple Stereoselective Synthesis of Unsaturated Lactone Intermediates and Their Conversion into Natural Dihydropyranones and Their Enantiomers#, Letters in Organic Chemistry 2013; 10 (5) . https://dx.doi.org/10.2174/1570178611310050003
DOI https://dx.doi.org/10.2174/1570178611310050003 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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