Humilisin E: Strategy for the Synthesis and Access to the Functionalized Bicyclic Core.
- Resource Type
- Academic Journal
- Authors
- Verma P; Department of Chemistry and NanoScience Center, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland.; Pallerla RR; Department of Chemistry and NanoScience Center, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland.; Rolig A; Department of Chemistry and NanoScience Center, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland.; Pihko PM; Department of Chemistry and NanoScience Center, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland.
- Source
- Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: PubMed not MEDLINE; MEDLINE
- Subject
- Language
- English
Humilisin E is a diterpenoid possessing a rare epoxidized cyclononene trans -fused with a bicyclo[3.2.0]heptane core. We have identified the P atropisomer of the corresponding cyclononadiene as a potential biosynthetic/synthetic precursor to humilisin E and reported two different strategies for the stereocontrolled synthesis of the appropriately functionalized bicyclic cores of humilisin E. The first route involves a Stork epoxynitrile cyclization via a Mg alkoxide, and the second, more stereoselective approach utilizes the Wolff rearrangement as the key step.