ChemInform Abstract: Relative and Absolute Stereochemistries and Total Synthesis of (+)-Macrosphelides A and B, Potent, Orally Bioavailable Inhibitors of Cell—Cell Adhesion.

✍ Scribed by T. SUNAZUKA; T. HIROSE; Y. HARIGAYA; S. TAKAMATSU; M. HAYASHI; K. KOMIYAMA; S. OMURA; P. A. SPRENGELER; A. B. III SMITH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199808227

✦ Synopsis

Relative and Absolute Stereochemistries and Total Synthesis of (+)-Macrosphelides A and B, Potent, Orally Bioavailable Inhibitors of Cell-Cell Adhesion.

-The relative and absolute stereochemistries of the title compounds (VI) and (VII) are determined by spectroscopic studies, single-crystal X-ray diffraction of (VI) and Mosher NMR method. The assignments are confirmed by a total synthesis of (VI), which starts with the condensation of the acid (I) and the alcohol (II), both obtained by asymmetric dihydroxylation of E,E-hexa-2,4-dienoic acid tert-butyl ester. Coupling with the third building block (IV) leads to (V), which undergoes macrolactonization. After deprotection (VI) is obtained, identical with the natural product. -