Premium
Artificial deoxy glycosides of anthracyclines
Author(s) -
Klaffke Werner,
Pudlo Peter,
Springer Dirk,
Thiem Joachim
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910193
Subject(s) - glycoside , chemistry , lewis acids and bases , glycosyl , allylic rearrangement , stereochemistry , organic chemistry , catalysis
Abstract In Lewis acid mediated allylic rearrangement reactions of L ‐rhamnal ( 1 ) and L ‐fucal ( 2 ) with daunomycinon ( 6 ) 2′‐deoxyhex‐2′‐enopyranosides have been obtained exclusively. Furthermore, glycals 1 and 4 have been treated with the glycosyl acceptors 6, 7 , and 9 and N ‐iodosuccinimide (NIS) to produce the corresponding α‐configurated 2′‐deoxy‐2′‐iodo glycosides. Among these, 16 represents a bis (glycoside) with both benzylic aglycon positions substituted. In none of the above cases has a substantial amount of β‐glycoside been detected. Attempts to convert ε‐isorhodomycinon ( 8 ) into a glycoside on a preparative scale, under Lewis acid conditions have been unsuccessful. However, the α‐glycoside 13 has been obtained by the Helferich method.