Stereocontrolled [3 + 2] annulations with arene chromium tricarbonyl complexes: construction of spirocyclic compounds related to fredericamycin A.
[reaction: see text] An efficient method has been developed for the stereocontrolled construction of polycyclic and spirocyclic compounds, including the spirocyclic core of the antitumor agent fredericamycin A. The strategy involves a one-pot aldol addition/Brook rearrangement/cyclization sequence beginning from arene chromium tricarbonyl complexes and can formally be described as a [3 + 2] annulation.
Moser
William H
WH
Department of Chemistry, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, USA. moser@chem.iupui.edu
Zhang
Jian
J
Lecher
Carl S
CS
Frazier
Tracy L
TL
Pink
Maren
M
D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D017608:Chromium Compounds / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000903:Antibiotics, Antineoplastic; D017608:Chromium Compounds; D007546:Isoquinolines; D007659:Ketones; D013141:Spiro Compounds; C016660:fredericamycin A