Natural Biological Source The Ho Pa Alkyl, Three Terpene Compounds And Their Method Of Isotope-labeled Analogues

Bacteriohopanoids represent a particularly important series of triterpenoids,widely distributed in bacteria.One of the common features of these pentacyclic hopanepolyols is the presence of an extended non-terpenoid and polyhydroxylated side-chain attached to the triterpenic moiety via a C-C bond.These hopanepolyols generally act as a membrane stabilizer in the bacteria which produce them.The further biological functions of these biohopanoids can also be addressed if one considers the broad diversity in both structures and functionalites found in the side-chain.Moreover,the stereochemistries of some of biohopanoids are still unconfirmed due to the lack of synthetic methodology to prepare them. Meanwhile,the biosynthetic pathways of these pentacyclic hopanepolyols are still not clear. More studies are needed for this domain.But the deuterated analogs of their naturally occurring products were the most useful materials for the biosynthetic studies.All the above mentioned demands need a facile synthetic strategy for these pentacyclic hopanepolyols.In this study,we describe a general methodology for the generation of the C-C bond between C₃₀-hopane and the C₅-polyhydroxylated carbohydrates derivative through an efficient preparation of a hopanyllithium intermediate which was generated through a LiDBB mediated reductive lithiation,and a hopanylcopper complex generated from a zero-valent copper or a mixed couprate.This new method enabled us to synthesize several polyhydroxylated biohopanoid derivatives.We have confirmed the stereochemistry of several natural hopanepolyols by the comparison of our newly synthetic molecules with the naturally occurred ones.On the other hand,the synthetic deuterated analog is using for the biosynthetic studies of a carbocyclic polyhydroxylated ether found in a eubacterium Zymomonas mobilis.The results of this study provide us an really more general approach for the chemical syntheses of these special natural compounds.It will facilate the studies on the structures, biofounctions and biosynthetic approaches of these polyhydroxylated biohopanoids.