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(6S)-Methyl-l-swainsonine [(1R,2S,6S,8S,8aS)-6-methyl­octa­hydro­indolizine-1,2,8-triol]

✍ Scribed by Håkansson, Anders E. ;Horne, Graeme ;Fleet, George W.J. ;Watkin, David J.

Publisher
International Union of Crystallography
Year
2006
Tongue
English
Weight
302 KB
Volume
63
Category
Article
ISSN
1600-5368

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✦ Synopsis

Methyl-l-swainsonine, C 9 H 17 NO 3 , together with the 6Repimer, was formed in a synthetic sequence in which there was an ambiguity in configuration at position C-6. This ambiguity was resolved by establishing the relative stereochemistry of the title compound by X-ray crystallographic analysis. The absolute configuration was determined by the use of dglycero-d-gulo-heptono-1,4-lactone as the starting material.

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The title tetracyclic compound, C 29 H 40 O 7 , has been obtained unexpectedly in a synthetic study of the natural diterpenoid, paclitaxel. There is an intramolecular OÐHÁ Á ÁO hydrogen bond between the hydroxy and benzyloxy groups.

Heterotricyclodecane XX (+)-(1S, 3S, 6S,
Heterotricyclodecane XX (+)-(1S, 3S, 6S, 8S)- und (−)-(1R, 3R, 6R, 8R)-2, 7-Dioxa-twista-4,9-dien
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**(+)‐(1__S__, 3__S__, 6__S__, 8__S__)‐ and (−)‐(1__R__, 3__R__, 6__R__, 8__R__)‐2,7‐dioxa‐twista‐4,9‐diene.** A synthesis and the determination of the sense of chirality of (+)‐(1__S__, 3__S__, 6__S__, 8__S__)‐ and (−)‐(1__R__, 3__R__, 6__R__, 8__R__)‐2,7‐dioxa‐twista‐4,9‐diene ((+)‐**5** and (−)‐

(1R,3R,4S)-8-Phenyl­menthyl (8S,9S)-8-fe
(1R,3R,4S)-8-Phenyl­menthyl (8S,9S)-8-ferrocenyl-6-methyl-1,4-di­thia-6-aza­spiro­[4,4]­nonane-9-carboxyl­ate
✍ García-Granda, Santiago ;Fernández-Rodríguez, Manuel A. ;Aguilar, Enrique ;Ferná 📂 Article 📅 2002 🏛 International Union of Crystallography 🌐 English ⚖ 214 KB

Single-crystal X-ray study T = 200 K Mean '(C±C) = 0.011 A Ê R factor = 0.054 wR factor = 0.142 Data-to-parameter ratio = 8.0 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.