Tetrahedron

Total synthesis of (±)-dysidiolide

D Demeke, CJ Forsyth

Index: Demeke, Damtew; Forsyth, Craig J Tetrahedron, 2002 , vol. 58, # 32 p. 6531 - 6544

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Citation Number: 25

Abstract

The total synthesis of (±)-dysidiolide was accomplished with a high level of intramolecular stereo-induction. Methylation of 6-carboethoxy-3-chloro-5-methyl-cyclohex-2-enone provided 33 bearing the 6, 7-trans-dimethyl substitution of the C6–C11 B-ring. Diastereoselective conjugate addition upon enone 34 installed the C11 stereogenic center. Annulation then provided an A-ring enone (23), a substrate for a challenging conjugate ...

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