Stereodivergent synthesis of diastereoisomeric carba analogs of glycal-derived vinyl epoxides: A new access to carbasugars
✍ Scribed by Ileana Frau; Valeria DI Bussolo; Lucilla Favero; Mauro Pineschi; Paolo Crotti
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 209 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
Abstract
A convenient method for the stereoselective synthesis of diasteroisomeric vinyl epoxides (−)‐2α and (−)‐2β, the carba analogs of D‐galactal and D‐allal‐derived vinyl epoxides 1αand 1β, has been elaborated starting from tri‐O‐acetyl‐D‐glucal. The key step of this synthesis is an application of the known Claisen thermal rearrangement of a glucal derivative, the vinyl allyl ether (+)‐3b, which allows to switch the glycal structure into the corresponding carba analog scaffold. Epoxides (−)‐2α and (−)‐2β derive from the same synthetic intermediate, the trans diol (+)‐5. Chirality, 2011. © 2011 Wiley‐Liss, Inc.