Studies On The Chemistry Of Tribenzotriquinacene And Total Synthesis Of Hyacinthacine A₆

This thesis is concerned with the studies on the chemistry of tribenzotriquinacene,a novel family of polycyclic hydrocarbon,novel cyclophane and a series of building blocks were synthesized,also including the first total synthesis of hyacinthacine A₆.It mainly consists of the following three parts:First,a review of literature on the synthesis of tribenzotriquinacene and its derivatives was revealed.In which the construction of tribenzotriquinacene and the extension were introduced in details,novel hydrocarbons were achieved on the extension at the different parts of tribenzotriquinacenes.In chapter 2,the study on the chemistry oftribenzotriquinacene was introduced in detail.An efficient method for the regioselective chlorornethylation of tribenzotriquinacenes was developed,and the hexakis-,Pentakis-(chloromethyl) tribenzotriquinacene were prepared as key interemediates,the first examples of novel bowl-shaped tribenzotriquinacenes bearing three dithiametacyciophane units within their arene peripheries were synthesized;which are host-molecules for the small guest-molecules.Additionally,an efficient method for the formylation of tribenzotriquinacenes was developed.Attempts to control of the amount of formylating agent were processed,and a series of interesting molecules,such as mono-,bis-,tris-substituted derivatives of tribenzotriquinacenes were synthesized:. Based on all of them,novel organic networks such as molecular container compounds, dendritic architectures and complex organometallic compounds become accessible.In Chapter 3,the first total synthesis of hyacinthacine A6 was described.Starting from the readily available D-glucose as the chiral pool,the chiral centers of D-glucose were well used and rebuilt,and two polyhydroxylated pyrrolidines were prepared with high yields and stereoselectivity.Thus,carbon-chain lengthening by a suitable functionalized two more carbon atoms fragment,followed by simultaneous reduction and intramolecular cyclization led to hyacinthacine A₆.