Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution

A. Rodríguez; M. Nomen; B. W. Spur; J. J. Godfroid; T. H. Lee

doi:10.1016/S0040-4020(00)00983-2

Total synthesis of 12(R)-HETE, 12(S)-HETE, ²H₂-12(R)-HETE and LTB₄ from racemic glycidol via hydrolytic kinetic resolution

A. Rodríguez
, M. Nomen
, B. W. Spur
, J. J. Godfroid
, T. H. Lee

Cell Biology

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

36 Scopus citations

Abstract

The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-²H₂]-12(R)-HETE and Leukotriene B₄ from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB₄.

Original language	English (US)
Pages (from-to)	25-37
Number of pages	13
Journal	Tetrahedron
Volume	57
Issue number	1
DOIs	https://doi.org/10.1016/S0040-4020(00)00983-2
State	Published - Jan 1 2001

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00983-2

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title = "Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution",

abstract = "The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.",

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T1 - Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution

AU - Rodríguez, A.

AU - Nomen, M.

AU - Spur, B. W.

AU - Godfroid, J. J.

AU - Lee, T. H.

PY - 2001/1/1

Y1 - 2001/1/1

N2 - The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.

AB - The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.

UR - https://www.scopus.com/pages/publications/0035056012

UR - https://www.scopus.com/pages/publications/0035056012#tab=citedBy

U2 - 10.1016/S0040-4020(00)00983-2

DO - 10.1016/S0040-4020(00)00983-2

M3 - Article

AN - SCOPUS:0035056012

SN - 0040-4020

VL - 57

SP - 25

EP - 37

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Total synthesis of 12(R)-HETE, 12(S)-HETE, ²H₂-12(R)-HETE and LTB₄ from racemic glycidol via hydrolytic kinetic resolution

Abstract

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