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

1 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

Access to Document

10.1016/0040-4020(78)88034-X

Cite this

@article{8334038806ce488fa0c7b9bc7f400682,

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

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.",

author = "Anderson, {Niels H.} and Tseng, {Chia Li W.} and Ana Moore and Yoshimoto Ohta",

year = "1978",

doi = "10.1016/0040-4020(78)88034-X",

language = "English (US)",

volume = "34",

pages = "47--52",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes

AU - Anderson, Niels H.

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 - http://www.scopus.com/inward/record.url?scp=0343737428&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343737428&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(78)88034-X

DO - 10.1016/0040-4020(78)88034-X

M3 - Article

AN - SCOPUS:0343737428

SN - 0040-4020

VL - 34

SP - 47

EP - 52

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this