Synthesis of griseolic acid B by pi-face-dependent radical cyclization

S Knapp; M R Madduru; Z Lu; G J Morriello; T J Emge; G A Doss

doi:10.1021/ol0167210

Synthesis of griseolic acid B by pi-face-dependent radical cyclization

Org Lett. 2001 Nov 1;3(22):3583-5. doi: 10.1021/ol0167210.

Authors

S Knapp¹, M R Madduru, Z Lu, G J Morriello, T J Emge, G A Doss

Affiliation

¹ Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, Piscataway, New Jersey 08854-8087, USA. knapp@rutchem.rutgers.edu

PMID: 11678714
DOI: 10.1021/ol0167210

Abstract

[reaction: see text]. Radical cyclization of 6 affords the bicyclic vinyl ether 9 with the appropriate stereochemistry for elaboration (seven steps) to griseolic acid B (1).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors
Adenosine / analogs & derivatives*
Adenosine / chemical synthesis*
Cyclization
Indicators and Reagents
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Phosphodiesterase Inhibitors / chemical synthesis*
Stereoisomerism
Streptomyces / chemistry

Substances

Indicators and Reagents
Phosphodiesterase Inhibitors
griseolic acid B
3',5'-Cyclic-AMP Phosphodiesterases
Adenosine