Cross-metathesis is synthetically equivalent to ( and has replaced ) a procedure of ozonolysis of an alkene to two ketone fragments followed by the reaction of one of them with a Wittig reagent.
12.
In this notation a Diels-Alder reaction is a ( 4 + 2 ) cycloaddition and a 1, 3-dipolar addition such as the first step in ozonolysis is a ( 3 + 2 ) cycloaddition.
13.
These metabolites have been confirmed as naturally occurring in human atherosclerotic arteries and are categorized into a class of secosterols termed " atheronals ", generated by ozonolysis of cholesterol's double bond to form a 5, 6 secosterol as well as a secondary condensation product via aldolization.
14.
The Ozonolysis gave aldehyde "'36 "'with ammonia converting the thioester into an amide group and aldehyde reduction ( sodium borohydride ) followed by mesylation and bromination ( lithium bromide ) gave the bromide "'37 "'with conversion of the amide group into a nitrile group as the completed AD section.
15.
Using intermediates 5 and 6, a Diels-Alder reaction produced a bicyclic compound ( 7 ) . 7 then underwent ozonolysis to open the six-membered ring leading to selenide ( 8 ) . 8 was then deselenated to form 9 ( E-9 and Z-9 ), lastly leading to the formation of (-) domoic acid.
16.
Both the cyclopentene ring and the cyclohexenone ring were oxidized next in an ozonolysis ( ozone ) forming triketone "'29 "', an aldol condensation of the 1, 5-dicarbonyl unit ( pyrrolidine acetate ) formed cyclohexene "'30 "'with tosylation of the oxime group, a second oxidation with periodic acid cleaves the cyclohexene ring and diazomethane esterifies the resulting carboxylic acid group in "'31 " '.
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