Simple Stereoselective Synthesis of Unsaturated Lactone Intermediates and Their Conversion into Natural Dihydropyranones and Their Enantiomers#

Author(s): Digambar Balaji Shinde, Boddu Shashi Kanth, Avula Satyakumar, V.T. Kamble, Biswanath Das.

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 5 , 2013

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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.

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Article Details

VOLUME: 10
ISSUE: 5
Year: 2013
Page: [317 - 323]
Pages: 7
DOI: 10.2174/1570178611310050003

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