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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 9
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Original Articles

Straightforward and Facile Synthesis of a Bioactive Component from Zingiber cassumunar Roxb.

, &
Pages 1212-1217 | Received 28 May 2013, Published online: 28 Mar 2014
 

Abstract

Straightforward and facile synthesis of a bioactive component A from Zingiber cassumunarRoxb. is described. The phenylbutenoid dimer A was reported to possess anti-inflammatory and cytotoxic activities. The optically active cyclohexene ring fragment was obtained via the highly diastereo- and enantioselective Diels–Alder reaction of chiral acryloyloxazolidinones (1a and 1b) and 1-(4-hydroxy-3-methoxyphenyl)butadiene (2). The enantiomeric excess of Diels–Alder adducts 3a and 3bwere determined via high-performance liquid chromatotography of the corresponding bis-acetate (6). The greatest enantiomeric excess (99.9% ee) was obtained when the 4-phenyloxazolidin-2-one (1a) chiral auxiliary was used in combination with TiCl4. The optically pure bioactive compound A was prepared from the optically active Diels–Alder adduct (3a) in two additional steps.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENT

The authors thank New Drug Development Research Institute and Central Laboratory of Kangwon National University for the use of analytical instruments and bioassay facilities.

Notes

a Reaction conditions: dienophile 1 (1.0 equiv), diene 2 (1.5 equiv), Et2AlCl (1.0 equiv), CH2Cl2, −78 °C, 5 h; or dienophile 1 (1.0 equiv), diene 2 (1.5 equiv), TiCl4 (1.0 equiv), CH2Cl2, −20 °C, 2 h.

b Isolated yield after chromatography.

c Based on the chiral HPLC analysis of diacetate 6.

d Not detected.

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