A solid-phase approach towards the development of 3-aza-6,8-dioxabicyclo[3.2.1]octane scaffolds.
The development of new strategies for solid-phase synthesis of 3-aza-6,8-dioxabicyclo[3.2.1]octane scaffolds, named BTKa, is described. The preparation was made possible by the combination of three components: amines, alpha-halo-acetophenones, and sugar or tartaric acid derivatives. By anchoring each of the three components it was possible to synthesize BTKa compounds either as amino alcohols or amido esters. The compatibility of the protocols with different classes of amines and substituted alpha-halo-acetophenones was demonstrated.
Trabocchi
Andrea
A
Dipartimento di Chimica Organica 'Ugo Schiff', Università degli Studi di Firenze, Polo Scientifico di Sesto Fiorentino, Via della Lastruccia 13, Sesto Fiorentino, Firenze, Italy.
Mancini
Francesco
F
Menchi
Gloria
G
Guarna
Antonio
A
D000098:Acetophenones / Q000737:chemistry / Q000378:metabolism; D000438:Alcohols / Q000737:chemistry; D000588:Amines / Q000737:chemistry / Q000378:metabolism; D000605:Amino Alcohols / Q000737:chemistry / Q000378:metabolism; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry / Q000378:metabolism
D000098:Acetophenones; D000438:Alcohols; D000588:Amines; D000605:Amino Alcohols; D001372:Aza Compounds; D004952:Esters; D009795:Octanes; D013644:Tartrates; C029768:tartaric acid; C026728:octane