A norbornyl route to cyclohexitols: stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

✍ Scribed by Goverdhan Mehta; Sripada Lakshminath

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 131 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00409-3

✦ Synopsis

A novel fragmentation sequence within the norbornane system, involving C 1 -C 7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised.