A nine-step total synthesis of (-)-platencin.

Abstract

Within 1 year, platencin, a recently discovered antibiotic, has become a highly competitive synthetic target, due to its promising bioactivity and its unusual complex molecular architecture. Herein, a particularly concise total synthesis of platencin starting from inexpensive perillaldehyde is described. The key features of this approach are (1) a highly diastereoselective Diels-Alder reaction with Rawal's dieneforming the first all-carbon quaternary center, (2) a ring-closing metathesis to generate the strained tricylic skeleton, (3) a hydration/dehydration strategy to efficiently shift the endocyclic alkene to the exoposition, and (4) a 1,4-addition of a hindered ketone enolate to methyl acrylate to create the second all-carbon quaternary center. In view of the brevity (nine linear steps) and the overall yield of 10%, our synthesis compares favorably with all the previous ones.

• Authors: Konrad Tiefenbacher, Johann Mulzer
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 74 Issue 8 Pg. 2937-41 (Apr 17 2009) ISSN: 1520-6904 [Electronic] United States
• PMID: 19260660 (Publication Type: Journal Article)

Chemical References

• Aminophenols
• Anti-Bacterial Agents
• Cycloparaffins
• Monoterpenes
• Polycyclic Compounds
• perillaldehyde
• platencin

Topics

• Aminophenols (chemical synthesis, chemistry)
• Anti-Bacterial Agents (chemical synthesis, chemistry)
• Catalysis
• Cyclization
• Cycloparaffins (chemical synthesis, chemistry)
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Monoterpenes (chemical synthesis, chemistry)
• Polycyclic Compounds (chemical synthesis, chemistry)
• Stereoisomerism