Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

Chang Hong Huo; Xiao Hui Su; Yu Fang Wang; Xi Ping Zhang; Qing Wen Shi; Hiromasa Kiyota

doi:10.1016/j.tetlet.2007.02.063

Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

Chang Hong Huo, Xiao Hui Su, Yu Fang Wang, Xi Ping Zhang, Qing Wen Shi, Hiromasa Kiyota

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

23 Citations (Scopus)

Abstract

A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2α,10β-diacetoxy-5α,9α,20α-trihydroxy-3α,11α;4α,12α;14α,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition.

Original language	English
Pages (from-to)	2721-2724
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2007.02.063
Publication status	Published - Apr 9 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.02.063

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@article{da44f6d2447544db87bfc9c645a66a86,

title = "Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis",

abstract = "A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2α,10β-diacetoxy-5α,9α,20α-trihydroxy-3α,11α;4α,12α;14α,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition.",

author = "Huo, {Chang Hong} and Su, {Xiao Hui} and Wang, {Yu Fang} and Zhang, {Xi Ping} and Shi, {Qing Wen} and Hiromasa Kiyota",

note = "Funding Information: The work reported in this Letter was financially supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, National Education Ministry of PR China to Q.-W.S.",

year = "2007",

month = apr,

day = "9",

doi = "10.1016/j.tetlet.2007.02.063",

language = "English",

volume = "48",

pages = "2721--2724",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "15",

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T1 - Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

AU - Huo, Chang Hong

AU - Su, Xiao Hui

AU - Wang, Yu Fang

AU - Zhang, Xi Ping

AU - Shi, Qing Wen

AU - Kiyota, Hiromasa

N1 - Funding Information: The work reported in this Letter was financially supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, National Education Ministry of PR China to Q.-W.S.

PY - 2007/4/9

Y1 - 2007/4/9

N2 - A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2α,10β-diacetoxy-5α,9α,20α-trihydroxy-3α,11α;4α,12α;14α,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition.

AB - A novel taxane with an unprecedented 5/5/4/6/6/6-membered hexacyclic skeleton containing [3.3.2]propellane was isolated from the needles of the Canadian yew, Taxus canadensis. The structure was established as 2α,10β-diacetoxy-5α,9α,20α-trihydroxy-3α,11α;4α,12α;14α,20-tricyclotaxan-13-one (1), which exists as two conformational isomers on the basis of spectroscopic analysis. This compound would be biogenetically derived from a normal 6/8/6-taxane by the intramolecular aldol reaction and [2+2] cycloaddition.

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SN - 0040-4039

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JO - Tetrahedron Letters

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ER -

Canataxpropellane, a novel taxane with a unique polycyclic carbon skeleton (tricyclotaxane) from the needles of Taxus canadensis

Abstract

ASJC Scopus subject areas

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