Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Synthesis of Biologically Active Compounds from Limonene
Kiyoshi SAKAIHiroshi SUEMUNE
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1988 Volume 46 Issue 4 Pages 334-343

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Abstract
Starting with (+) - and (-) -limonenes as chiral synthons, syntheses of biologically active compounds such as prostaglandins, (+) -brefeldin A and nepetalactones have been studied. The key-step of these conversions is based on the stereoselective cyclization of 3, 4-disubstituted 4-pentenals into cis-3, 4-disubstituted cyclopentanones using the Rh (I) -complex.
Ring cleavage and reconstruction of five and six membered rings under acetalization conditions are also discussed.
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© The Society of Syhthetic Organic Chemistry, Japan
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