Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose

Yuguo Du; Jun Liu; Robert J. Linhardt

doi:10.1021/jo051644y

Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose

Yuguo Du, Jun Liu, Robert J. Linhardt

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

57 Scopus citations

Abstract

The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC₅₀ = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.

Original language	English
Pages (from-to)	1251-1253
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	71
Issue number	3
DOIs	https://doi.org/10.1021/jo051644y
State	Published - 3 Feb 2006
Externally published	Yes

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title = "Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose",

abstract = "The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC50 = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.",

author = "Yuguo Du and Jun Liu and Linhardt, {Robert J.}",

year = "2006",

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doi = "10.1021/jo051644y",

language = "English",

volume = "71",

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journal = "Journal of Organic Chemistry",

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AU - Du, Yuguo

AU - Liu, Jun

AU - Linhardt, Robert J.

PY - 2006/2/3

Y1 - 2006/2/3

N2 - The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC50 = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.

AB - The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC50 = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 10 linear steps with 25.7% overall yield.

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DO - 10.1021/jo051644y

M3 - Article

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VL - 71

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JF - Journal of Organic Chemistry

IS - 3

ER -

Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose

Abstract

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