Enantioselective synthesis of (−)-conduramine C1 and aminobromocyclitol derivatives

✍ Scribed by Susy Allemann; Pierre Vogel

• Book ID: 102857335
• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: German
• Weight: 708 KB
• Volume: 77
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19940770103

✦ Synopsis

Abstract

(1__S__,2__R__,6__R__,7__R__)‐4‐Phenyl‐3,10‐dioxa‐5‐azatricyclo[5.2.1.0^2,6^]dec‐4‐en‐9‐one ((+)‐5) obtained in 6 steps from the Diels‐Alder adduct of furan to 1‐cyanovinyl (1__S__)‐camphanate ((+)‐3) was reduced to the corresponding endo‐alcohol (−)‐6 the treatment of which with HBr/AcOH provided (−)‐(3a__S__,4__S__,6__R__,7__S__,7a__R__)‐4β‐bromo‐3aβ,4,5,6,7,7aβ‐hexahydro‐2‐phenyl‐1,3‐benzoxazole‐6β,7α‐diyl diacetate ((−)‐17). Elimination of HBr with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) and acidic hydrolysis furnished (−)‐(1__R__,2__S__,3__R__,4__R__)‐4‐aminocyclohex‐5‐ene‐1,2,3‐triol (  (−)‐conduramine C~1~;(−)‐1).