Abstract
In this thesis, we investigated the synthesis of nature product Simplexins A which was an eunicellin (cladiellin) diterpene. We prepared enone 109 from piene 110 via two tandem reactions. Treatment of compound 109 with side chain 130 underwent 1,4-addition and iodination to yield α-iodo ketone 108. We used atom-transfer cycloaddition as the key step to constract the cis-hydrindanone. The compound 123 was obtained through double bond migration and [1,5] hydride shift. The five-member ring of compound 123 was cleavaged by ozonolysis to give compound 125 containing a ketone and an aldehyde group. Despite compound 125 would react with methanol solvent and gave hemiacetal compound 124. Fortunately, we could get compound 125 again by using trifluoroacetic acid. Using ethylene glycol to protected the highly reactive aldehyde gave compound 126. Furthermore, the aldol reaction of compound 134 with acrolein was carried out and generated compound 127. Compound 127 could be an intermediate and have applications to the total synthesis of Simplexins A.