123064-89-1

Upstream product

• 133401-01-1 isobatzelline A 
• 233609-57-9 6-chloro-7-methoxy-1-methyl-2-methylsulfanyl-3,4-dihydro-1H-pyrrolo[4,3,2-de]quinolin-8-one 
• 175792-33-3 6-chloro-5-formyl-1,3,4,5-tetrahydro-7,8-dimethoxy-1-methylpyrrolo<4,3,2-de>quinoline 
• 233609-55-7 6-chloro-1,3,4,5-tetrahydro-7,8-dimethoxy-1-methyl-2-methylthiopyrrolo<4,3,2-de>quinoline 
• 233609-54-6 6-chloro-5-formyl-1,3,4,5-tetrahydro-7,8-dimethoxy-1-methyl-2-methylthiopyrrolo<4,3,2-de>quinoline 

Downstream Products

• 146555-78-4 makaluvamine A 
• 138683-68-8 damirone B 

Relevant academic research and scientific papers

Divergent Total Syntheses of Isobatzellines A/B and Batzelline A

Divergent total syntheses of isobatzellines A/B and batzelline A were accomplished. A fully substituted common indole intermediate bearing C-2 methylthio and C-5 chloro groups was constructed via ring expansion of benzocyclobutenone oxime sulfonate with NaSMe and a benzyne-mediated cyclization/functionalization sequence as the key steps. The total synthesis of isobatzelline B was achieved via formation of the iminoquinone structure by the redox-neutral acid-promoted C-5 proto-dechlorination of the common indole intermediate. The total syntheses of isobatzelline A and batzelline A were completed in a divergent manner by oxidation of the common indole intermediate using MnO2 or Mn(OAc)3, respectively.

Syntheses of batzelline A, batzeline B, isobatzelline A, and isobatzelline B

Batzellines A and B (1a, b) and isobatzellines A and B (2a, b) are 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline-containing marine alkaloids characterized by the presence of a methylthio substituent at C-2 of the tricyclic system. We describe here the tota