81558-18-1Relevant academic research and scientific papers
Phyllanthostatin 1-Phyllanthoside Orthoacid Rearrangement
Pettit, George R.,Cragg, Gordon M.,Suffness, Matthew
, p. 5060 - 5063 (1985)
Solvolysis of phyllanthoside (1b) in 1:9 ethanol-water (14 days at room temperature) consumed about 54percent of the starting glycoside and afforded the S3'-monoacetyl derivative 1f and phyllanthostatins 1 (1a) and 4 (1e) in 8-10percent yields accompanied by five related products of orthoacid rearrangement and/or deacetylation.Several additional minor transformation products were detected by HPLC analyses.When phyllathostatin 1 (1a) was subjected to the same solvolysis reaction for 21.5 h, approximately half rearranged to phyllanthoside (1b).After 4 days the product composition resembled that from phyllanthoside.Discovery of the phyllanthostatin 1 phyllanthoside orthoacid rearrangement revealed a very important aspect of Phyllanthus glycoside chemistry and provided the first examples of O-3 O-4 acetyl migrations in a glucopyranoside.
Phyllanthoside-Phyllanthostatin Synthetic Studies. 9. Total Syntheses of (-)-Phyllanthostatin 1, (+)-Phyllanthostatin 2, and (+)-Phyllanthostatin 3
Smith III, Amos B.,Hale, Karl J.,Vaccaro, Henry A.,Rivero, Ralph A.
, p. 2112 - 2122 (2007/10/02)
Phyllanthostatins 1, 2, and 3 (2-4) have been synthesized for the first time. The unusual 1′→2β glycosidic linkages of the disaccharide moieties were constructed via anchimerically-assisted Koenigs-Knorr reactions. The novel β-glycosyl esters were then ge
THE TOTAL SYNTHESIS OF (+)-PHYLLANTHOSTATIN 2
Smith, Amos B. III,Hale, Karl J.,Vaccaro, Henry A.
, p. 5591 - 5594 (2007/10/02)
The first total synthesis of the antitumor glycoside phyllanthostatin 2 (3) is reported utilizing a Mitsunobu glycosidation protocol to unite the disaccharide and aglycone moieties.
