A FORMAL TOTAL SYNTHESIS OF (t)-QUADRONE

C Iwata, M Yamashita, S Aoki, K Suzuki, I Takahashi…

Index: Iwata; Yamashita; Aoki; et al. Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 1 p. 436 - 439

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Citation Number: 8

Abstract

This article deals with a formal total synthesis of (t)~ quadrone (1), an antitumor sesquiterpene. The cyclopentenone (1) was trans—formed into cyclopropane derivative (g), a regioselective reductive ring opening of which and trapping of the enolate intermediate (lg) by a C—1 unit afforded the diquinaneacetate (11). By a two—step sequence ll was converted into methyl (1R*, 5R*, 6R*)—6—(2—hydroxyethyl)—7, 7-dimethyl—2— ...