Reactivity of Tricarbonyl(pentadienyl)iron(1+) Cations: Enantioselective Synthesis of 5-HETE Methyl Ester

Authors

Chunlin Tao, Marquette University
William Donaldson, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

1993

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

The syntheses of racemic 5-HETE methyl ester (1) and of 5-HETE lactone (5-HL) were accomplished in 11 steps from tricarbonyl [l-(methoxycarbonyl)pentadienyl]iron(l+) hexafluorophosphate (2). A second synthesis of 1 from 2 in five steps was also achieved. Starting with optically active 5 the synthesis of (+)-l and (-)-l in high optical purity was realized. The stereochemistry of the 6,8-diene portion and the stereochemistry of the C5 asymmetric center of 1 were controlled by the (tricarbonyl)- iron adjunct.

Comments

The Journal of Organic Chemistry, Vol. 58, No. 8, (1993): 2134-2143. DOI.

Recommended Citation

Tao, Chunlin and Donaldson, William, "Reactivity of Tricarbonyl(pentadienyl)iron(1+) Cations: Enantioselective Synthesis of 5-HETE Methyl Ester" (1993). Chemistry Faculty Research and Publications. 854.
https://epublications.marquette.edu/chem_fac/854