ChemInform Abstract: Platinum(II)‐Catalyzed Generation and [3 + 2] Cycloaddition Reaction of α,β‐Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds.

Abstract

Platinum(II)-Catalyzed Generation and [3 + 2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds. -(SAITO, K.; SOGOU, H.; SUGA, T.; KUSAMA, H.; IWASAWA*, N.; J. Am. Chem. Soc. 133 (2011) 4, 689-691, http://dx.

All-carbon [3 + 2] cycloaddition in natural product synthesis

“…all-carbon [3 + 2] cycloaddition, for instance, Berson's and Little's [3 + 2] cycloaddition through diyl trapping with an olefin [14,15] and Trost's palladium-catalyzed trimethylenemethane cycloaddition [16], which allows the preparation of five-membered carbocycles, have been emerged since the 1970s. Thereafter, many novel and important all-carbon [3 + 2] cycloaddition reactions, such as the phosphine-catalyzed [3 + 2] cycloaddition [17], platinum-catalyzed [3 + 2] cycloaddition [18], and Rhodium-catalyzed [3 + 2] cycloaddition [12], were invented and have been extensively used in natural product synthesis in the last decade. Many reviews focusing the method development of the all-carbon [3 + 2] cycloaddition have been published [19][20][21].…”

“…The platinum-catalyzed intermolecular [3 + 2] cycloaddition of propargyl ether derivatives and vinyl ether producing polycyclic indoles was disclosed by Iwasawa and co-workers in 2011 [18,66] In 2020, Ye and co-workers used a platinum-catalyzed intramolecular [3 + 2] cycloaddition of a propargylic ketal derivative to complete the total synthesis of Kopsia indole alkaloids [67] (Scheme 11). The platinum-catalyzed intramolecular [3 + 2] Scheme 12: (A) Synthesis of phyllocladanol (21) features a Lewis acid-catalyzed formal intramolecular [3 + 2] cross-cycloaddition of cyclopropane 1,1-diesters with alkenes [68].…”