1370332-24-3Relevant academic research and scientific papers
Enantioselective syntheses of rigidiusculamides A and B: Revision of the relative stereochemistry of rigidiusculamide A
Chen, Gui-Yang,Huang, Huang,Ye, Jian-Liang,Wang, Ai-E,Huang, Hui-Ying,Zhang, Hong-Kui,Huang, Pei-Qiang
, p. 504 - 518 (2012)
The first enantioselective synthesis of cytotoxic natural products rigidiusculamides A (ent-21) and B (8) has been achieved by two synthetic routes. The first one is convergent based on the common intermediate 11, obtained through a high yielding SmI2-mediated Reformatsky-type reaction. A highly diastereoselective one-pot Dess-Martin periodinane-mediated bis-oxidation allowed the direct conversion of the diastereomeric mixture of 11 into rigidiusculamide B (8). Isolation of minor diastereomer 21, in combination with computational work, allowed us to suggest the structure of the natural rigidiusculamide A to be ent-21, as synthesized by the second route. Four diastereomers (7, ent-7, 22 a, and 22 b) and an enantiomer (21) of rigidiusculamide A (ent-21) have been synthesized. On the basis of literature precedents and computational work, a biosynthetic pathway for rigidiusculamides A and B was proposed to account for the opposite configuration at C-5 of those two congeners.
