The first syntheses of four stereoisomeric diaminocyclooctane diols, as well as a chlorocyclooctane aminodiol, are reported. In the first part, photooxygenation of cis,cis-1,3-cyclooctadiene gave a bicyclic endoperoxide, which was reduced with zinc followed by mesylation of the hydroxyl groups. Treatment with sodium azide afforded 1,4- and 1,2-cyclooctene diazides. Oxidation of the double bonds in the isomeric diazides with OsO₄, followed by hydrogenation of the azide groups, led to 3,8-diaminocyclooctane-1,2-diol and 3,4-diaminocyclooctane-1,2-diols. In the second part, cis-3,8-diazidocyclooctene was converted into the corresponding epoxide. Stereospecific hydrolysis of the epoxide ring with HCl_(g) in methanol, and hydrogenation of the azide groups gave 3,8-diamino-2-chloro-cyclooctan-1-ol. Bromination of the double bond in cyclooctene diacetate, followed by acetate deprotection, azidolysis of the bromides, and hydrogenation of the azide groups resulted in the formation of 2,3-diaminocyclooctane-1,4-diol.

报道了四种立体异构体二氨基环辛烷二醇以及氯环辛烷氨基二醇的首次合成。在第一部分中，顺式，顺式-1,3-环辛二烯的光氧合反应生成了双环内过氧化物，该环氧化物被锌还原，随后被羟基甲磺酸化。用叠氮化钠处理得到1，4-和1，2-环辛烯二叠氮化物。用OsO ₄氧化异构二叠氮化物中的双键，然后叠氮化物进行氢化，生成3,8-二氨基环辛烷-1,2-二醇和3,4-二氨基环辛烷-1,2-二醇。在第二部分中，将顺式-3，8-二叠氮基环辛烯转化为相应的环氧化物。HCl对环氧环的立体定向水解_（g）在甲醇中，叠氮化物基团加氢得到3，8-二氨基-2-氯-环辛-1-醇。环辛烯二乙酸酯中双键的溴化，然后进行乙酸酯脱保护，溴化物的叠氮化和叠氮化物基团的氢化导致形成2,3-二氨基环辛烷-1,4-二醇。