Stereoselective synthesis of substituted gamma-butyrolactones by the [3+2] annulation of allylic silanes with chlorosulfonyl isocyanate: enantioselective total synthesis of (+)-blastmycine.
[structure: see text]. A stereoselective synthesis of gamma-butyrolactones by the [3 + 2] annulation of allylic silanes with N-chlorosulfonyl isocyanate (CSI) was developed. An enantioselective total synthesis of (+)-blastmycinone was accomplished using this annulation as the key step.
Peng
Z H
ZH
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D017953:Isocyanates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D000900:Anti-Bacterial Agents; D017953:Isocyanates; D012821:Silanes; C416059:blastomycinone; D015107:4-Butyrolactone