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The rarity of native LTB and the lack of a detailed structural assignment have prompted various studies dealing with detection, activity, structural identification, and synthesis of this important compound, The Harvard group (48,49,55-57) was the first to report the complete elucidation of its structure as well as the preparation of gram quantities of L T B 4 by an effi­ cient, stereoselective total synthesis. Structure Elucidation and Total Synthesis of the Leukotrienes 45 When LTA 4 methyl ester 35 is treated with mild acid or exposed to silica gel, six diastereomeric dihydroxy-7,9,ll,14-eicosatetraenoic acids are ob­ tained, four of which are 5,6-diols that are readily cleaved by treatment with aqueous periodate.

A minireview summarizing various biological data to date has appeared (145). The rarity of native LTB and the lack of a detailed structural assignment have prompted various studies dealing with detection, activity, structural identification, and synthesis of this important compound, The Harvard group (48,49,55-57) was the first to report the complete elucidation of its structure as well as the preparation of gram quantities of L T B 4 by an effi­ cient, stereoselective total synthesis. Structure Elucidation and Total Synthesis of the Leukotrienes 45 When LTA 4 methyl ester 35 is treated with mild acid or exposed to silica gel, six diastereomeric dihydroxy-7,9,ll,14-eicosatetraenoic acids are ob­ tained, four of which are 5,6-diols that are readily cleaved by treatment with aqueous periodate.

0-Hz coupling constant for 7 5 6. Four-carbon chain extension by reaction with l-lithio-4ethoxybutadiene, mesylation of the resultant secondary alcohol, and vinyl ether hydrolysis and elimination afforded crystalline dienal 34. Wittig con­ densation of dienal 34 and ylide 17 afforded LTA 4 methyl ester 35 in 35% yield after purification on triethylamine-deactivated silica gel. The epoxytetraene 35 was found to be extremely acid-sensitive but could be safely stored frozen in a benzene matrix in the presence of triethylamine.

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Introduction to acid-base chemistry(en)(19s) by Lower S. K.


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