Enantioselective synthesis of (−)‐conduramine C1and aminobromocyclitol derivatives
作者:
Susy Allemann,
Pierre Vogel,
期刊:
Helvetica Chimica Acta
(WILEY Available online 1994)
卷期:
Volume 77,
issue 1
页码: 1-9
ISSN:0018-019X
年代: 1994
DOI:10.1002/hlca.19940770103
出版商: WILEY‐VCH Verlag GmbH
数据来源: WILEY
摘要:
Abstract(1S,2R,6R,7R)‐4‐Phenyl‐3,10‐dioxa‐5‐azatricyclo[5.2.1.02,6]dec‐4‐en‐9‐one ((+)‐5) obtained in 6 steps from theDiels‐Alderadduct of furan to 1‐cyanovinyl (1S)‐camphanate ((+)‐3) was reduced to the correspondingendo‐alcohol (−)‐6the treatment of which with HBr/AcOH provided (−)‐(3aS,4S,6R,7S,7aR)‐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 (−)
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