𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The [2,3] Wittig rearrangement of tertiary allylic ethers. Application to the synthesis of the C12C25 subunit of zincophorin

✍ Scribed by Michael Balestra; Mark D Wittman; James Kallmerten

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
253 KB
Volume
29
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Ketone 4 representing the C12-C25 subunit of the ionophore antibiotic zincophorin, has been prepared by a sequence incorporating the [2,3] Wittig rearrangement of a tertiary allylic ether and subsequent lactonization via intramolecular, acid-catalyzed SN' addition to an allylic ether.

📜 SIMILAR VOLUMES

Olefinic stereoselection in the [2,3]-Wi
Olefinic stereoselection in the [2,3]-Wittig rearrangement of α,β-disubstituted allylic ethers forming trisubstituted olefins
✍ Katsuhiko Tomooka; Tatsuya Igarashi; Naoyuki Kishi; Takeshi Nakai 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 237 KB

The F\_,/Z-selectivities in the [2,3]-Wittig rearrangements of secondary 13-(methyl or silyl)allylic ethers are shown to depend critically on the nature of groups on the carbanion terminus, thereby permitting elucidation of the structural requirements for attaining high Z-selectivity.

ChemInform Abstract: The Dienolate [2,3]
ChemInform Abstract: The Dienolate [2,3]-Wittig Rearrangement — Diastereoselective Synthesis of Highly Functionalized Tertiary Alcohols.
✍ Martin Hiersemann; Christa Lauterbach; Annett Pollex 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 37 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Advances in the vinylogous Mukaiyama ald
Advances in the vinylogous Mukaiyama aldol reaction and its application to the synthesis of the C1C7 subunit of oleandolide
✍ Jorma Hassfeld; Markus Kalesse 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 106 KB

The synthesis of a stereo pentade of the macrolide antibiotic oleandolide is reported. The C1 C7 fragment resembles the analogous segment of Panek's total synthesis of oleandolide. The use of the vinylogous Mukaiyama aldol reaction shortens the route significantly and has the advantage of utilizing