Syntheses of optically pure conduramines via the strategy of hetero Diels-Alder reaction of masked o-benzoquinones with homochiral nitroso dienophiles.
Highly stereoselective hetero Diels-Alder reactions of masked o-benzoquinones (MOBs) with homochiral nitroso dienophiles are described along with their application in the syntheses of (+)-ent-conduramine F-1, (+)-conduramine E-1, (-)-conduramine A-1, (+)-conduramine A-1 tetraacetate, and (-)-ent-conduramine A-1 tetraacetate.
Lu
Ping-Hsun
PH
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
Yang
Ching-Shun
CS
Devendar
Badugu
B
Liao
Chun-Chen
CC
D016227:Benzoquinones / Q000737:chemistry*; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C514594:6-aminocyclohex-4-ene-1,2,3-triol; D016227:Benzoquinones; D003511:Cyclohexanols; D003514:Cyclohexylamines; C545152:conduramine A-1; C545151:conduramine E