• Cycloartenol toBuxus alkaloids

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      https://www.ias.ac.in/article/fulltext/jcsc/093/06/1015-1030

    • Keywords

       

      Cycloartenol; Buxus alkaloids; cyclolaudenol; side-chain degradation; reductive alkylation; Buxandonine; cycloprotobuxine-F; cycloprotobuxine-A; cyclobuxophyllinine-M; Schenk oxidation; pyridinium chromate-on-silica gel; cycloeucalanone; 31-Norcyclo-laudenone

    • Abstract

       

      Cycloartenol, a pentacyclic triterpene alcohol, has emerged as an obligatory intermediate in the biosynthesis of sterols in higher plants and algae. Cycloartenol has also been implicated in the biosynthesis of steroidal alkaloids. TheBuxus alkaloids, which have a pregnane-type framework, are considered to arise from cycloartenol by catabolic processes with nitrogen incorporation at an appropriate stage, although no biosynthetic studies appear to have been carried out. Thus, cycloartenol is an important substrate in nature for elaborating a rather large group of secondary metabolites. In an effort to mimic some of these processes in the laboratory, we have carried out transformations of cycloartenol intoBuxus alkaloids. New routes for side-chain degradation of cycloartenol and cyclolaudenol have been developed. A novel method for functionalization at C-16 has been worked out and a new strategy for regioselective oxygenation of 4-methyl has been exploited. Synthesis of buxandonine, cycloprotobuxine-F, cycloprotobuxine-A, cyclobuxophyllinine-M and 31-norcyclolaudenone have been achieved.

    • Author Affiliations

       

      Sukh Dev1

      1. Malti-Chem Research Centre, Nandesari, Vadodara - 391 340, India
    • Dates

       
  • Journal of Chemical Sciences | News

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