Stereospecific synthesis of (+/-)-1,2-anhydro methyl rocaglate.
The rocaglates and analogues thereof have recently become targets for synthesis because of their potent antitumor activity. One of the major difficulties has been the control of stereochemistry of the adjacent -Ph and -An groups. In this letter we show that 14 is converted into 5 as a single stereoisomer and subsequently transformed into 1,2-anhydro methyl rocaglate 20. [reaction: see text]
Magnus
Philip
P
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA. p.magnus@mail.utexas.edu
Stent
Matthew A H
MA
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C511470:1,2-anhydro methyl rocaglate; D000972:Antineoplastic Agents, Phytogenic; D001572:Benzofurans