✦ LIBER ✦
D-Erythronolactone and 2,3-O-Isopropylidene-L-erythrose as C4 Building Units: An Efficient Synthesis of both Enantiomers ofendo-Brevicomin and its 7-Vinyl Analogues
✍ Scribed by Gypser, Andreas ;Flasche, Michael ;Scharf, Hans-Dieter
- Book ID
- 102901985
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 618 KB
- Volume
- 1994
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
Both enantiomers of endo‐brevicomin (+)‐ and (−)‐3a were synthesized from D‐erythronolactone (1) and 2,3‐O‐isopropylidene‐L‐erythrose (2), respectively. In the course of the synthesis also the 7‐vinyl analogues (+)‐ and (−)‐3b of endo‐brevicomin are available. The key step of the synthesis is the diastereoselective acetalization of the diols 1 and 10 with 4‐(phenylsulfonyl)‐2‐butanone (4) and boron trifluoride‐diethyl ether complex as a catalyst. The described procedure yields the key compounds 5a and ent‐7b in good yields and with high diastereomeric purity. magnified image