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2004
Other natural products
U 0800
Versatile Asymmetric Synthesis of the Kavalactones: First Synthesis of
— Simple and efficient approaches are developed. The first one utilizes
45- 231 (+)-Kavain.
aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/
decarboxylation reaction. The second one shows that the previously developed substrates (XV) can be transformed into the kavalactone ring system in a one-pot procedure. The reaction is demonstrated for the racemic system. The tin-substituted intermediates [cf. (XIc)] serve as advanced general precursors of kavalactone derivatives via
Pd(0)-catalyzed Stille couplings with aryl halides. The first asymmetric synthesis of
(+)-kavain (XIa) is completed in 64% overall yield in three steps from cinnamaldehyde.
— (SMITH*, T. E.; DJANG, M.; VELANDER, A. J.; DOWNEY, C. W.; CARROLL,
K. A.; VAN ALPHEN, S.; Org. Lett. 6 (2004) 14, 2317-2320; Dep. Chem., Williams
Coll., Williamstown, MA 01267, USA; Eng.) — Steudel
2004
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