Structures of Two Novel Sesquiterpenoids Formed by the Lead Tetraacetate Oxidation of β-Caryophyllene

Toshikazu UCHIDA; Yoshiharu MATSUBARA; Yuzo KOYAMA

doi:10.1271/bbb1961.53.3011

Agricultural and Biological Chemistry

Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369

Structures of Two Novel Sesquiterpenoids Formed by the Lead Tetraacetate Oxidation of β-Caryophyllene

Toshikazu UCHIDA, Yoshiharu MATSUBARA, Yuzo KOYAMA

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JOURNAL FREE ACCESS

1989 Volume 53 Issue 11 Pages 3011-3015

DOI https://doi.org/10.1271/bbb1961.53.3011

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Abstract

Two crystalline minor products (14 and 15) were newly obtained by the oxidation of β-caryophyllene (1) with lead tetraacetate. The structures were determined as 4, 4-dimethyltricyclo-[6.3.2.0^{2, 5}]tridec-8-en-1-ol (14) and 4, 4-dimethyl-9-oxatetracyclo[6.4.2.0^{2, 5}.0^{8, 10}]tridecan-1-ol (15) by HR-MS, LR-MS, IR, ¹H-NMR, ¹³C-NMR, and single crystal X-ray analysis data. Products 14 and 15 are novel sesquiterpenes.

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