Synthesis of a C4-epi-C1-C6 fragment of FR901464 using a novel bromolactolization.
[reaction: see text] A synthesis of a C4-epi-C1-C6 fragment of the antitumor agent FR901464 is reported. The advanced intermediate prepared in this study contains two of the three correct stereocenters found in the C1-C6 moiety of FR901464. For the preparation of this intermediate, we have developed a highly diastereoselective bromolactolization of a delta-alkenyl ketone.
Albert
Brian J
BJ
Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, USA.
Koide
Kazunori
K
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001966:Bromine / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis
D000970:Antineoplastic Agents; C104486:FR 901464; D007783:Lactones; D011714:Pyrans; D013141:Spiro Compounds; D001966:Bromine