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The first total synthesis and neurotrophic activity of clusiparalicoline A, a prenylated and geranylated biaryl from Clusia paralicola

✍ Scribed by Shigeki Takaoka; Kousuke Nakade; Yoshiyasu Fukuyama

Book ID
104251940
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
120 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The first synthesis of clusiparalicoline A, a prenylated and geranylated biphenyl compound isolated from the roots of Clusia paralicola, has been achieved by applying the sequential palladium-catalyzed Stille and Suzuki reactions to the formation of all the C C bonds on electron-rich aryl bromide and triflate. Clusiparalicoline A has been found to exhibit a potent neurite outgrowth promoting activity at 1.0 mM in a primary culture of fetal rat cortical neurons.

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## Abstract The first total synthesis of naturally occurring mappain has been achieved by a convergent sequence. The key strategy involved in the synthesis of mappain was a (__E__)‐stilbene formation by __Horner__–__Wadsworth__–__Emmons__ reaction of the corresponding prenylated benzaldehyde with a