Strategic Development Towards The Synthesis Of Eudesmane Sesquiterpenoids

This thesis aims at the development of a new strategy for the total synthesis of eudesmane sesquiterpenoids and we have achieved the first total synthesis of6β,14-epoxyeudesm-4(15)-en-1β-ol. It consists of the following four chapters.Chapter1summarized the intramolecular Diels-Alder reactions of furans (1MDAF) and applications of the IMDAF in total synthesis of natural products was reviewed in detail.In Chapter2, a novel strategic approach towards the total synthesis of eudesmane sesquiterpenoids was presented. We developed a new strategic approach to eduesmanolides via an IMDAF as the key step in which all carbons in the skeleton of eduesmanolides were introduced in a diasteroselective manner. This approach was applied in the first total synthesis of6β,14-epoxyeudesm-4(15)-en-1β-ol (1), a naturally occurring C-1, C-14oxygenated eudesmane sesquiterpenoid.Chapter3described our study toward the asymmetric synthesis of eudesmane sesquiterpenoids based on our new strategic approach by using (R)-1-(4-methoxyphenyl)ethanamine as an effective chiral auxiliary.Chapter4described the total synthesis of cis-allohedycaryol starting from a functionalized oxabicyclic template as an extension of our group's synthetic approach of eudesmane sesquiterpenoids.