Highly Stereoselective Total Synthesis of the Natural Leukotriene (-)-(5S,6S)-LTA₄Methyl Ester and of Its η-7-10 (Tricarbonyl) Iron Complex

Transition metal complexes in organic synthesis. Part 47.1 Organic synthesis via tricarbonyl(η4-diene)iron complexes

“…9 This method was applied to an enantioselective total synthesis of the natural leukotriene (2)-5(S),6(S)-LTA 4 methyl ester (18) (Scheme 5). 10 Friedel-Crafts acylation of the enantiopure iron complex of trans-penta-2,4-dienoic 2,2,2-trichloroethyl ester 15 using the acid chloride of adipic acid monomethyl ester afforded complex 17 which was subsequently converted to the LTA 4 methyl ester 18.…”

Additions to Fe(CO)3−Dienal Complexes: Dependence of Diastereoselectivity on Lewis Acid

“…Conversely, hydride reduction of ketone-substituted complexes (X = O, Y = alkyl) appears to occur via anti-addition to the s-cis conformation ( 1a ), leading to 2 (X = O, Y = alkyl, Z = H), with excellent (>95:5) selectivity. ,,, Preference for the s-cis conformation in this case has been attributed to the presence of significant steric interactions in the s-trans conformation between the alkyl substituent (Y) and the substituent at the C 2 position of the diene complex (R 2 ).…”

Preparation of Organometallic Complexed Sugars: Hetero Diels−Alder Reactivity of Tricarbonyl(formyltrimethylenemethane)- iron

“…Such compounds have been examined for use in carbonyl metallo immunoassays (CMIA) using FT-IR spectroscopy leukotrienes, and carbohydrates have also been reported. σ-Bonded manganese and iron carbonyl complexes of carbohydrates have been prepared by displacement of 1-glucosyl halides or 6-deoxy-6-haloglucosides.…”