Total synthesis of aeruginosin DA495A

• Grant number: 15/12547-0
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: September 01, 2015
• End date: June 30, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ronaldo Aloise Pilli
• Grantee: Henrique Magri Marçon
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The project aims for the developmento of the first total synthesis of aeruginosin DA495A, natural product recently isolated from the cianobacteria Mycrocistis aeruginosa, whose biological activity was not widely evaluated. Its structure was proposed based on spectroscopic analysis and chromatographic comparation of derivatizated fragments (HPLC). The aeruginosins, in general, present a tetrapeptide scaffold of unusual aminoacids and derivates. The most characteristic fragment is a 2-carboxy-6-hydroxioctahydroindole (Choi) found in a cis relative configuration but may differ on absolute configurations in C-2, C-6 and the bridge head carbons. This convergent synthetic approach proposal may provide the synthesis of the structure atributed to aeruginosina DA495A as its analogues.