𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Cyclobutanones for the stereoselective synthesis of bifunctional macrolide intermediates

✍ Scribed by G Fráter; U Müller; W Günther

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
181 KB
Volume
25
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Beckmann fragmentation of the oximes 5 and 6 respectiveZy, which were derived from -the cyclobutanones Sand 5, furnished the bifunctional five carbon units 7 and g with ea. 98% -and 91% stereoselectivity. We were interested for some time in the possible control of vicinal stereochemistry in open chain compounds2. A most successful approach to this task turned out to be the controlled aldol-reaction3. The more classical way to meet this problem is to stereoselectively construct a cyclic intermediate, which subsequently can be converted into an open chain compound.

📜 SIMILAR VOLUMES

Stereoselective synthesis of the cytotox
Stereoselective synthesis of the cytotoxic macrolide aspergillide B
✍ Santiago Díaz-Oltra; César A. Angulo-Pachón; María N. Kneeteman; Juan Murga; Mig 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 274 KB

A total, stereoselective synthesis of the cytotoxic macrolide aspergillide B has been performed. A cross metathesis and a C-glycosidation via a Mukaiyama-type aldol reaction were key features of the synthesis. The macrocyclic lactone ring was created by means of the Yamaguchi procedure.

Studies in macrolide synthesis: A stereo
Studies in macrolide synthesis: A stereocontrolled synthesis of a (9S)-macrolide intermediate for oleandomycin using chiral boron reagents.
✍ Ian Paterson; M.Anne Lister; Roger D. Norcross 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 350 KB

The (9s)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone ($2. The Cl-C7 and Q-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)-and (-)-(Ipc)zBOTf, respectively. Conventional reduction conditions using