Total Synthesis of All Stereoisomers of Dihydrokawain andDihydrokawain-5-ol

Abstract

A short total synthesis of all stereoisomers of dihydrokawain and dihydrokawain-5-ol has been achieved. Key steps include a condensation of 3-phenylpropanal with chiral allenylboronic esters and the HgO-catalyzed addition of MeOH to the 5-hydroxy-7-phenylhept-2-ynoic acid. This synthesis afforded (＋)-dihydrokawain in 72% and (＋)-dihydrokawain-5-ol in 19% overall yields respectively.

Key words: dihydrokawain, dihydrokawain-5-ol, chiral allenylboronic ester, total synthesis

Cite this article

QUAN Wei-Guo^a, YU Bin-Xun^a, SU Ying-Peng^a, SHE Xue-Gong*^,a,b
PAN Xin-Fu*^{,a. Total Synthesis of All Stereoisomers of Dihydrokawain andDihydrokawain-5-ol[J]. Chin. J. Org. Chem., 2007, 27(12): 1516-1519.}

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Dihydrokawain和Dihydrokawain-5-ol及其立体异构体的全合成