Hydroxycyclopentanone derivatives from D-Mannose via ring closing metathesis: An improved synthesis of a key intermediate of Tricyclo-DNA

Vonlanthen, DavidDavidVonlanthenLeumann, ChristianChristianLeumann0000-0002-7996-70832024-10-232024-10-232003https://boris-portal.unibe.ch/handle/20.500.12422/133056A large scale, 10 step synthesis of cyclopentanone 1 , starting from the chiral pool compound D-mannose, is described. The synthesis proceeds via a ring closing metathesis reaction as the key step in an overall yield of 23%. Cyclopentanone 1 is a central intermediate for the synthesis of tricyclo-DNAenlarge-scale synthesis tricyclo-DNA500 - Science::570 - Life sciences; biology500 - Science::540 - ChemistryHydroxycyclopentanone derivatives from D-Mannose via ring closing metathesis: An improved synthesis of a key intermediate of Tricyclo-DNAarticle10.7892/boris.6856110.1055/s-2003-39177