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1 article(s) from Vosloo, Hermanus C.M.

Metathesis access to monocyclic iminocyclitol-based therapeutic agents

Ileana Dragutan,
Valerian Dragutan,
Carmen Mitan,
Hermanus C.M. Vosloo,
Lionel Delaude and
Albert Demonceau

Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81

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Graphical Abstract

Scheme 1: Well-defined Mo- and Ru-alkylidene metathesis catalysts.

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Scheme 2: Representative pyrrolidine-based iminocyclitols.

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Scheme 3: Synthesis of (±)-(2R*,3R*,4S*)-2-hydroxymethylpyrrolidin-3,4-diol (18), (±)-2-hydroxymethylpyrrolid...

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Scheme 4: Synthesis of enantiopure iminocyclitol (−)-(2S,3R,4S,5S)-2,5-dihydroxymethylpyrrolidin-3,4-diol (23...

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Scheme 5: Synthesis of 1,4-dideoxy-1,4-imino-D-allitol (29) and formal synthesis of (2S,3R,4S)-3,4-dihydroxyp...

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Scheme 6: Synthesis of iminocyclitols 35 and 36.

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Scheme 7: Total synthesis of iminocyclitols 40 and 44.

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Scheme 8: Synthesis of 2,5-dideoxy-2,5-imino-D-mannitol [(+)-DMDP] (49) and (−)-bulgecinine (50).

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Scheme 9: Synthesis of (+)-broussonetine G (53).

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Scheme 10: Structural features of broussonetines 54.

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Scheme 11: Synthesis of broussonetines by cross-metathesis.

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Scheme 12: Representative piperidine-based iminocyclitols.

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Scheme 13: Total synthesis of 1-deoxynojirimycin (62) and 1-deoxyaltronojirimycin (65).

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Scheme 14: Synthesis by RCM of 1-deoxymannonojirimycin (63) and 1-deoxyallonojirimycin (66).

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Scheme 15: Total synthesis of (+)-1-deoxynojirimycin (62).

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Scheme 16: Synthesis of ent-1,6-dideoxynojirimycin (83) and 5-amino-1,5,6-trideoxyaltrose (84).

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Scheme 17: Synthesis of 1-deoxygalactonojirimycin (64), 1-deoxygulonojirimycin (91) and 1-deoxyidonojirimycin (...

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Scheme 18: Synthesis of L-1-deoxyaltronojirimycin (96).

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Scheme 19: Synthesis of 1-deoxymannonojirimycin (63) and 1-deoxyaltronojirimycin (65).

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Scheme 20: Synthesis of 5-des(hydroxymethyl)-1-deoxymannonojirimycin (111) and 5-des(hydroxymethyl)-1-deoxynoj...

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Scheme 21: Synthesis of D-1-deoxygulonojirimycin (91) and L-1-deoxyallonojirimycin (122).

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Scheme 22: Total synthesis of fagomine (129), 3-epi-fagomine (126) and 3,4-di-epi-fagomine (130).

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Scheme 23: Total synthesis of (+)-adenophorine (135).

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Scheme 24: Total synthesis of (+)-5-deoxyadenophorine (138) and analogues 142–145.

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Scheme 25: Synthesis by RCM of 1,6-dideoxy-1,6-iminoheptitols 148 and 149.

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Scheme 26: Synthesis by RCM of oxazolidinyl azacycles 152 and 154.

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Scheme 27: Representative azepane-based iminocyclitols.

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Scheme 28: Synthesis of hydroxymethyl-1-(4-methylphenylsulfonyl)azepane 3,4,5-triol (169).

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Scheme 29: Synthesis by RCM of tetrahydropyridin-3-ol 171 and tetrahydroazepin-3-ol 173.

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Album

Review

Published 27 May 2011

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