Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B4 (3-OH-LTB4) and analogues

Kamlesh Chauhan; Rama K. Bhatt; J R Falck; Jorge H. Capdevila

doi:10.1016/S0040-4039(00)73170-4

Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B₄ (3-OH-LTB₄) and analogues

Kamlesh Chauhan, Rama K. Bhatt, J R Falck, Jorge H. Capdevila

Biochemistry

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

17 Scopus citations

Abstract

3(S)-Hydroxy-Leukotriene B₄ (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral β-hydroxylactones 7/9.

Original language	English (US)
Pages (from-to)	1825-1828
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(00)73170-4
State	Published - Mar 21 1994

Keywords

Rieke zinc
Wittig
chelation-controlled reduction
eicosanoid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)73170-4

Cite this

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abstract = "3(S)-Hydroxy-Leukotriene B4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral β-hydroxylactones 7/9.",

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T1 - Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B4 (3-OH-LTB4) and analogues

AU - Chauhan, Kamlesh

AU - Bhatt, Rama K.

AU - Falck, J R

AU - Capdevila, Jorge H.

PY - 1994/3/21

Y1 - 1994/3/21

N2 - 3(S)-Hydroxy-Leukotriene B4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral β-hydroxylactones 7/9.

AB - 3(S)-Hydroxy-Leukotriene B4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral β-hydroxylactones 7/9.

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KW - Wittig

KW - chelation-controlled reduction

KW - eicosanoid

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