The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes

Niels H. Anderson; Chia Li W. Tseng; Ana Moore; Yoshimoto Ohta

doi:10.1016/0040-4020(78)88034-X

The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes

Niels H. Anderson
, Chia Li W. Tseng
, Ana Moore
, Yoshimoto Ohta

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The barbatenes (e.g. 3) and a number of other sesquiterpenes afford a novel rearrangement product on treatment with CF₃CO₂H. This substance, designated isobarbatene, is shown to have structure 6, the result of a bicyclo-[3.2.1]→[2.2.2]→[3.2.1] rearrangement followed by an exo Me shift and deprotonation. The structure assignment is based on spectral and chiroptical data for olefin 6 and its degradation products 8,9 and 10.

Original language	English (US)
Pages (from-to)	47-52
Number of pages	6
Journal	Tetrahedron
Volume	34
Issue number	1
DOIs	https://doi.org/10.1016/0040-4020(78)88034-X
State	Published - 1978
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4020(78)88034-X

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abstract = "The barbatenes (e.g. 3) and a number of other sesquiterpenes afford a novel rearrangement product on treatment with CF3CO2H. This substance, designated isobarbatene, is shown to have structure 6, the result of a bicyclo-[3.2.1]→[2.2.2]→[3.2.1] rearrangement followed by an exo Me shift and deprotonation. The structure assignment is based on spectral and chiroptical data for olefin 6 and its degradation products 8,9 and 10.",

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year = "1978",

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AU - Tseng, Chia Li W.

AU - Moore, Ana

AU - Ohta, Yoshimoto

PY - 1978

Y1 - 1978

N2 - The barbatenes (e.g. 3) and a number of other sesquiterpenes afford a novel rearrangement product on treatment with CF3CO2H. This substance, designated isobarbatene, is shown to have structure 6, the result of a bicyclo-[3.2.1]→[2.2.2]→[3.2.1] rearrangement followed by an exo Me shift and deprotonation. The structure assignment is based on spectral and chiroptical data for olefin 6 and its degradation products 8,9 and 10.

AB - The barbatenes (e.g. 3) and a number of other sesquiterpenes afford a novel rearrangement product on treatment with CF3CO2H. This substance, designated isobarbatene, is shown to have structure 6, the result of a bicyclo-[3.2.1]→[2.2.2]→[3.2.1] rearrangement followed by an exo Me shift and deprotonation. The structure assignment is based on spectral and chiroptical data for olefin 6 and its degradation products 8,9 and 10.

UR - https://www.scopus.com/pages/publications/0343737428

UR - https://www.scopus.com/pages/publications/0343737428#tab=citedBy

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ER -

The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes

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