Application of Modern Pummerer Methodology in Model Studies Toward the Total Synthesis of Palau’amine

Open Access
Author:
Li, Jianfeng
Graduate Program:
Chemistry
Degree:
Master of Science
Document Type:
Master Thesis
Date of Defense:
January 30, 2009
Committee Members:
  • Scott Trent Feldman, Thesis Advisor
  • Ken S Feldman, Thesis Advisor
Keywords:
  • Pummerer Reaction
Abstract:
A route leading to two key Pummerer substrates which bear a syn or trans cyclopentane moiety was designed, developed and completed as a model study toward the total synthesis of palau’amine. The Pummerer cyclization of the syn substrate was performed. The structure of the cyclized products was characterized and their stereochemistry was tentatively demonstrated base on the nOe effect. The Pummerer cyclization of the trans substrate was performed but a better way to isolate and characterize the product is needed. A route leading to two key Pummerer substrates which bear a cyclohexane/cyclohexene moiety and their cyclization is still under exploration.