A short and efficient stereoselective synthesis of all four diastereomers of sphingosine

Jae Mok Lee, Hyun-Suk Lim, Sung Kee Chung

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.

Original languageEnglish (US)
Pages (from-to)343-347
Number of pages5
JournalTetrahedron Asymmetry
Volume13
Issue number4
DOIs
StatePublished - Mar 22 2002
Externally publishedYes

Fingerprint

Sphingosines
Sphingosine
Serine
Derivatives
synthesis

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

A short and efficient stereoselective synthesis of all four diastereomers of sphingosine. / Lee, Jae Mok; Lim, Hyun-Suk; Chung, Sung Kee.

In: Tetrahedron Asymmetry, Vol. 13, No. 4, 22.03.2002, p. 343-347.

Research output: Contribution to journalArticle

@article{640c918a01d349ba8620892f3f825b35,
title = "A short and efficient stereoselective synthesis of all four diastereomers of sphingosine",
abstract = "Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.",
author = "Lee, {Jae Mok} and Hyun-Suk Lim and Chung, {Sung Kee}",
year = "2002",
month = "3",
day = "22",
doi = "10.1016/S0957-4166(02)00118-0",
language = "English (US)",
volume = "13",
pages = "343--347",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

T1 - A short and efficient stereoselective synthesis of all four diastereomers of sphingosine

AU - Lee, Jae Mok

AU - Lim, Hyun-Suk

AU - Chung, Sung Kee

PY - 2002/3/22

Y1 - 2002/3/22

N2 - Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.

AB - Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected α′-amino enone derivative 5 with NaBH4 and reduction of the free α′-amino enone derivative 7 with Zn(BH4)2.

UR - http://www.scopus.com/inward/record.url?scp=0037155732&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037155732&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(02)00118-0

DO - 10.1016/S0957-4166(02)00118-0

M3 - Article

VL - 13

SP - 343

EP - 347

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 4

ER -