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Synthesis 1997; 1997(9): 1061-1066
DOI: 10.1055/s-1997-1299
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A New Stereocontrolled Synthesis of the Racemic Forms of Savinin and Gadain

Renzo Rossi*
  • *Dipartimento di Chimica e Chimica Industriale, Università di Pisa, via Risorgimento 35, I-56126 Pisa, Italy, Fax +39(50)918260; E-mail: rossi@server1.dcci.unipi.it
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Publication Date:
31 December 2000 (online)

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A concise stereocontrolled synthesis of the racemic forms of two naturally occurring lignans, savinin (5) and gadain (6), is described. The reaction sequences used for the preparation of these lignans involve: (i) a regioselective and stereospecific Pd-mediated reaction between (3,4-methylenedioxy)phenylzinc chloride (15a) and the easily available methyl (Z)- and (E)-2,3-dibromopropenoate [(Z)- and (E)-(14)], respectively; (ii) a Pd-mediated reaction between the 3-aryl substituted 2-propenylzinc chloride (17) and the stereoisomerically pure 3-aryl-2-bromopropenoates (Z)- and (E)-16, respectively, so obtained; and (iii) treatment of the resulting dienyl esters (E)- and (Z)-18, with dicyclohexylborane followed by oxidation with 30% H2O2 in the presence of alkali and subsequent lactonization.

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