Synthesis of methyl 4-methyltricyclo[5.2.2.01,5]undec-4-ene-9-carboxylate, a possible precursor of isoeremolactone

Publication Type
Contribution to conference
Authors
Kraus, W.; Spitzner, D.; Sawitzki, G.; Weber, W.
Year of publication
1981
Published in
Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Prod., [Proc.]
Editor
Atanasova, B., Bulg. Acad. Sci
Series/labeling
3
Page (from - to)
610-11
Conference name
Int. Conf. Chem. Biotechnol. Biol. Act. Nat. Prod. 1st
Conference location
Sofia, Bulg.
Conference date
nnb
Abstract

Diels-Alder reaction of I with H2C:CHCO2Me gave 40% of a mixt. of tricycloundecanes contg. II (R = Me3C, X = O) which after dithiane ketalization and redn. gave 96% alc. II (R = H, X = H2). Dehydration of the latter with 85% H2SO4 gave the isoeremolactone precursor III, which could also be obtained by solvolysis of II (R = tosyl, X = H2).

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