A symmetry-driven approach to the putative spiroketal core of the didemnaketals

作者：Davy Jason A; Moreau Benoit; Oliver Allen G; Wulff Jeremy E^*

来源：Tetrahedron, 2015, 71(18): 2643-2657.

DOI：10.1016/j.tet.2015.03.043

• Didemnaketal synthesis
• Asymmetric synthesis
• Desymmetrization
• Cyclononenones
• Spiroketals

Didemnaketals A and B are isolation artifacts whose exact structures have been the subject of recent controversy. Although the biological function of the presumed progenitor-didemnaketal C-remains unknown, both degradation products are inhibitors of HIV protease, and are believed to function through an unusual dissociative mechanism. Other didemnaketals (D and E) have antibacterial activity. As a step towards better understanding the chemistry and biology of the didemnaketals, this report describes the efficient asymmetric synthesis of their putative spiroketal core from a meso-precursor.

• 出版日期2015-5-6