✦ LIBER ✦

New chiral building blocks from 1,2;5,6-di-O-isopropylidene-D-mannitol: Synthesis ofC2-symmetrical and unsymmetrical mono- and bisepoxides and of a polyhydroxylated butenolide

✍ Scribed by Mulzer, Johann ;Pietschmann, Catarina ;Schöllhorn, Bernd ;Buschmann, Jürgen ;Luger, Peter

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 694 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1995199508194

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The enantiopure epoxides 2–6 were synthesized from 1,2;5,6‐di‐O‐isopropylidene‐D‐mannitol (1). The terminal epoxides 2 and 3 are available from the desoxy mannitol 9 in three steps. The C~2~‐symmetrical epoxides 4 and 5 were generated via the C‐4‐inverted alcohol 15. The C~2~‐symmetrical bisepoxide 6 was prepared in a short sequence maintaining the symmetry throughout the entire synthesis. The crystalline butenolide 44 was prepared in five steps from 1 by Wittig olefination and lactonization.

📜 SIMILAR VOLUMES

Some new aspects of the synthesis and is

Some new aspects of the synthesis and isolation of 1,2:5,6-di-O-isopropylidene-d-mannitol

✍ Gordon J.F. Chittenden 📂 Article 📅 1991 🏛 Elsevier Science 🌐 English ⚖ 344 KB

1,2:5,6-Di-0-isopropylidene-o-mannitol (1) is the most important source of o-glyceraldehyde derivatives which are usedIe widely in synthesis. The formation of 1 from o-mannitol (2) has been studied severally"5. All of the syntheses require the separation of 1 from the accompanying 1,2:3,4:5,6\_tria