10.1002/hlca.200890211
The present study aimed to develop a practical and highly regio- and stereoselective method for the synthesis of oligoisoprenols, essential precursors for the synthesis of biologically important isoprenoids. The convergent synthetic strategy described is characterized by iterative allyl-allyl couplings of monomers derived from commercially available geraniol and repeated reductive elimination of p-toluenesulfonyl (Ts) groups. The study successfully demonstrated the use of this approach to synthesize (all-trans)-oligoisoprenols, such as (all-trans)-octaprenol and (all-trans)-decaprenol, which is more efficient and practical compared to previous methods. The key chemicals used in the process include geraniol, p-toluenesulfonyl, allyl bromide, allyl sulfone, and various reducing agents such as Li/EtNH2, Na/EtOH, Na/naphthalene, and LiHBEt3/Pd(dppp)Cl2. The study concluded that the developed convergent strategy is an effective method for the synthesis of long linear polyprene backbones.
10.1055/s-2004-835663
The study presents a novel methodology for synthesizing N-diphenylmethylene-2-vinyl-substituted cyclopropylamines, which are significant in pharmaceuticals and natural products due to their biological activity. The synthesis begins with allylsulfones, specifically compound 11, which can be obtained in both enantiomeric forms. The researchers utilized various chemicals, including base treatments for allylsulfones to form trans:cis cyclopropanols, and molecular modeling to study the stereoselectivity of cyclopropane formation. The study also involved the use of Garner’s aldehyde, a key intermediate in synthesizing biologically active compounds, and the transformation of amino alcohols into cyclopropylamines with the help of protecting groups like Tosyl, Boc, Moc, and benzyl. The purpose of these chemicals was to achieve high diastereoselectivity in the synthesis of chiral amino-cyclopropanes, which are valuable as building blocks for the synthesis of conformationally restricted amino acids. The study's innovative approach and findings contribute to the field of asymmetric synthesis, particularly for cyclopropylamines.