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Stereodivergent synthesis of diastereoisomeric carba analogs of glycal‐derived vinyl epoxides: A new access to carbasugars
Author(s) -
Frau Ileana,
Bussolo Valeria DI,
Favero Lucilla,
Pineschi Mauro,
Crotti Paolo
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21003
Subject(s) - chemistry , glycal , organic chemistry , stereochemistry , stereoselectivity , combinatorial chemistry , catalysis
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 1α and 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.