Total Synthesis of Peloruside A through Kinetic Lactonization and Relay Ring-Closing Metathesis Cyclization Reactions

Autor: Troy D. Ryba, Thomas R. Hoye, Junha Jeon, Manomi A. Tennakoon, Yini Wang, Lucas C. Kopel
Rok vydání: 2010
Předmět:
Zdroj: Angewandte Chemie International Edition. 49:6151-6155
ISSN: 1433-7851
DOI: 10.1002/anie.201002293
Popis: A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 4, which comprises C1–C9 of 1, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone 20, which embodies C13–C19. A new isomer of 1, the valerolactone iso-peloruside A (iso-1), was identified.
Databáze: OpenAIRE