Synthesis of an Advanced Intermediate of the Jatrophane Diterpene Pl-4: A Dibromide Coupling Approach

Abstract

The preparation of an advanced intermediate toward the synthesis of the jatrophane diterpene Pl-4 is described. The key step is a regioselective chelation-controlled lithiation of the (Z)-configured bromide in the corresponding vinyl dibromide precursor. The method outlined within this Article is suitable for the facile access of sterically hindered internal vinyl halides for further coupling reactions.

Bromine-lithium exchange on gem-dibromoalkenes part 1: batch vs microflow conditions

“…R = MOM). 5 Carbenoids of this type have occasionally been used in synthesis, 5,6 though most lithium/bromine vinyl carbenoids 2 are used in FBW rearrangements (Corey-Fuchs protocol) and knowledge of their properties remains fragmentary. The use of vinyl carbenoids 2 would provide a means to quickly build a trisubstituted alkene bearing a bromine atom and with a defined configuration, opening up many synthetic possibilities.…”

Copper-Catalyzed Highly Enantioselective 1,4-Protoboration of Terminal 1,3-Dienes

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Usually, basic main-group organometallics, such as organolithium or Grignard reagent, are necessary for traditional methods to make allylboranes. [19][20][21][22][23][24][25] The disadvantage of these strategies is their incompatibility with electrophilic functional groups. Since it was initially demonstrated by Suzuki and coworkers, catalytic 1,4-addition of 1,3-dienes using boron reagents has become a powerful synthetic tool to obtain allylic boronate systems (Figure 1a).…”

Enyne Metathesis Approach towards the Cyclopentane Motif of Jatrophane Diterpenes

“…Additionally, only a few routes to jatrophane diterpenes have been reported so far. [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]…”