𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of 3-amino sugars of the daunosamine type through hetero-Diels-Alder reaction of enaminones

✍ Scribed by Lutz F Tietze; Edgar Voß

Book ID
104219505
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
220 KB
Volume
27
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The thermally induced hetero-Diels-Alder reaction of vinyl ethers 2a-d and Nacylenaminones 3a-h leads to the diastereomeric adducts 4a-h and 5a-h in 75 -98 % yield providing cis-compounds 4a-h as the main products. Isomerisation of 4a-f with Lewis acids gives theXermodynamically more stable 5a-f. Transformation of 4 and 5 by hydrogenation leads to 3-amino sugar glycosides. Variation of the sugar moiety in anthracycline antibiotics, which are of great value in the

📜 SIMILAR VOLUMES

Synthesis of (±)-ramulosin via inverse t
Synthesis of (±)-ramulosin via inverse type hetero-diels-alder reaction 1
✍ Klaus Vogt; Richard R. Schmidt 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 822 KB

Condensatiar of 4-formylbutanoates (4 thloacetone (5) pcwided the 1 -oxa-1,3-dlene 4Ji?l,Y,',',",,p,"ni1i which afforded in high yielding inverse type hetero-Dlels-Am& reactions vith vinyl ethers and ketene acetals the desired dihydropyran cycloadducts 78-c and lla-c, respectively. Ttx? target molec