106499-65-4Relevant academic research and scientific papers
Synthetic studies directed toward naturally occurring tetramic acids. 3. Synthesis of (-)-methyl ydiginate and the tetramic acid subunit for streptolydigin
Boeckman Jr., Robert K.,Potenza, Joan C.,Enholm, Eric J.
, p. 469 - 472 (1987)
A concise stereocontrolled and enantioselective synthesis of the N-glycosylated tetramic acid subunit 2 required for streptolydigin (1) is described. Key features of the convergent synthesis include the condensation of aminosuccinimide 3 with pyrrolidinorhodinose 16 to β-glycosylamine 17 and eventual elaboration of tetramic acid 2 by a Dieckmann condensation. The structure and absolute stereochemistry of 17 was confirmed by correlation with (-)-methyl ydiginate (4) and its 4′-O-acetyl derivative 19, previously obtained from a major degradation product of natural streptolydigin (1).
