66529-66-6

Upstream product

• 225514-18-1 tert-butyl-(2-phenylsulfanyl-1-vinyl-but-3-enyl)-amine 
• 225514-19-2 Benzyl-(2-phenylsulfanyl-1-vinyl-but-3-enyl)-amine 
• 225514-16-9 Isopropyl-(2-phenylsulfanyl-1-vinyl-but-3-enyl)-amine 
• 225514-17-0 methyl-(2-phenylsulfanyl-1-vinyl-but-3-enyl)-amine 

Relevant academic research and scientific papers

Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (?)-Cyclosmenospongine

We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (?)-cyclosmenospongine. A highly convergent three-component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters in a single operation proceeding in a highly efficient manner to give exclusively the trans-decalin framework. In addition, we found that the enol ether geometry and the relative configuration of C3 and C8 are crucial for the success of the polyene cyclization.

[1,3] And [3,3] rearrangements of 3-amino-1,5-hexadienes: Solvent effect on the regioselectivity

3-Amino-1,5-Hexadienes rearrange under anionic conditions to give a [1,3] product in addition to the [3,3] (Cope) product. With some substrates the regioselectivity of the reaction is strongly influenced by the solvent polarity.