Issue 4, 1979

Structure and absolute stereochemistry of the sesquiterpene alcohol (–)-myliol: X-ray analysis of the p-bromobenzoate

Abstract

The structure and absolute configuration of the novel sesquiterpene alcohol, (–)-myliol (C15H22O) have been determined by X-ray analysis of its p-bromobenzoate (III). Crystals of the p-bromobenzoate (III) are triclinic, space group P1, a= 10.37(1), b= 10.20(1), c= 10.39(1)Å, α= 107.8(1), β= 71.6(1), γ= 110.3(1)°, Z= 2, with two independent molecules in an asymmetric unit. The structure was solved by the heavy-atom method, and refined by block-diagonal least-squares to R 0.085 over the 1 956 independent observed reflections. The absolute configuration was determined by the anomalous dispersion effect. The two molecules in the asymmetric unit have similar geometries, and each contains a novel fused 5,3,6,3-tetracyclic ring system. The two cyclopropane rings in this fused ring are in conjugation and the central cyclopropane ring conjugates further with an exo-double bond. The cyclopentane ring in this skeleton has an envelope conformation and the cyclohexane ring is considerably distorted by the two fused cyclopropane rings.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1979, 514-518

Structure and absolute stereochemistry of the sesquiterpene alcohol (–)-myliol: X-ray analysis of the p-bromobenzoate

H. Nozaki, J. Chem. Soc., Perkin Trans. 2, 1979, 514 DOI: 10.1039/P29790000514

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