Download PDF
Synthesis 1997; 1997(9): 1061-1066
DOI: 10.1055/s-1997-1299
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

savinin