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Synthesis 1993; 1993(4): 375-377
DOI: 10.1055/s-1993-25866
short paper
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Highly Efficient Synthesis of the Natural Spiro-Terpenoid (±)-Andirolactone

Arturo Orduña* , L. Gerardo Zepeda, Joaquín Tamariz
  • *Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, IPN, Prol. Carpio y Plan de Ayala, 11340 México D. F.
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Publikationsdatum:
17. September 2002 (online)

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A synthesis of the natural terpenoid spirolactone (±)-andirolactone (1) is described. Condensation of dimethyl malonate (9) with 1-acetyl-4-methyl-3-cyclohexen-1-ol (3), prepared by Diels-Alder reaction of olefin 5 and isoprene (4), and thermal decarboxylation of the resulting spirolactone 10, afforded 1 in 46 % overall yield.