Abstract
Inspired by the potent polycyclic xanthone antibiotic lysolipin I, a general study
on asymmetric dihydroxylation reactions of variously substituted isoquinolinones was
performed. Different isoquinolinones were efficiently prepared, either by a Pomeranz–Fritsch
type condensation or a Curtius rearrangement. Under a broad variety of conventional
oxygenation procedures, they proved very unreactive. However, either by suitable substitution
of the appending aromatic ring or more forcing conditions a dihydroxylation could
finally be performed, which allowed the synthesis of the EF-ring of lysolipin I.
Key words
lysolipin I - Pomeranz–Fritsch cyclization - Curtius rearrangement - asymmetric dihydroxylation
- isoquinolinone
