1982
DOI: 10.1016/s0040-4039(00)88671-2
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A total synthesis of leukotriene F4 (LTF4)

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Cited by 6 publications
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“…89 The azabicycloheptane skeleton was constructed from (143) by reduction of the azide with chromium(I1) chloride followed by treatment with sodium hydride and work-up with trifluoroacetic anhydride. Oxidation of (144) with sodium periodate followed by Pummerer rearrangement afforded the corresponding aldehyde, which was subsequently elaborated to the allylic alcohols (145) and (146). Only the (15S)-epimer (146) showed contractile activity on isolated rat aorta; however, neither (145) nor ( 146) was proaggregatory to human platelets.…”
Section: The Synthesis Of Analoguesmentioning
confidence: 99%
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“…89 The azabicycloheptane skeleton was constructed from (143) by reduction of the azide with chromium(I1) chloride followed by treatment with sodium hydride and work-up with trifluoroacetic anhydride. Oxidation of (144) with sodium periodate followed by Pummerer rearrangement afforded the corresponding aldehyde, which was subsequently elaborated to the allylic alcohols (145) and (146). Only the (15S)-epimer (146) showed contractile activity on isolated rat aorta; however, neither (145) nor ( 146) was proaggregatory to human platelets.…”
Section: The Synthesis Of Analoguesmentioning
confidence: 99%
“…The total synthesis of the LTF4 (227) has been reported by the Glaxo research group. 145 The protected glutamylcysteine diester (254) (prepared in six steps) was coupled to ( +)-LTA, methyl ester by an established method to afford, on deprotection, a diastereoisomeric mixture of LTF,.…”
Section: Leukotriene Bmentioning
confidence: 99%