Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 13, Issue 8, Pages 2927-2933Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2005.02.007
Keywords
(R)-goniothalamin; asymmetric synthesis; cytotoxic activity; cancer cells
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The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of alpha-benzyloxyacetaldehyde (2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde (12), followed by ring-closing metathesis are reported. The anti proliferative activities of (R)-1 and its Z-isomer 10 as well as of the synthetic dihydropyranone intermediates 7 and 8 against eight different cancer cell lines are also described. (c) 2005 Elsevier Ltd. All rights reserved.
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