Synthesis of (+)-isofagomine

The synthesis of (+)-isofagomine 1 using 4-pentenol 3 as a chiral precursor is described herein.

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(S)-2-((R)-1-(Benzyloxy)pent-4-en-2-yl)-1,4-dioxaspiro[4.5]decaneC20H28O3[α]D21=-1.5 (c 1.53, CHCl3)Absolute configuration: (2R, 2′S)Source of chirality: d-glyceraldehyde

(R,E)-5-(Benzyloxy)-4-((S)-1,4-dioxaspiro[4.5]decan-2-yl)pent-2-en-1-yl acetateC22H30O5[α]D21=-0.4 (c 0.93, CHCl3)Absolute configuration: (4R, 2′S)Source of chirality: d-glyceraldehyde

(R,E)-5-(Benzyloxy)-4-((S)-1,4-dioxaspiro[4.5]decan-2-yl)pent-2-en-1-olC20H28O4[α]D20=-11.2 (c 0.67, CHCl3)Absolute configuration: (4R,2′S)Source of chirality: d-glyceraldehyde

(S)-2-((R,E)-5-Azido-1-(benzyloxy)pent-3-en-2-yl)-1,4-dioxaspiro[4.5]decaneC20H27N3O3[α]D28=-8.5 (c 1.80, CHCl3)Absolute configuration: (2R,2′S)Source of chirality: d-glyceraldehyde

(S)-2-((R)-1-((2R,3R)-3-(Azidomethyl)-1,4-dioxaspiro[4.5]decan-2-yl)-2-(benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decaneC26H37N3O5[α]D27=+40.1 (c 1.33, MeOH)Absolute configuration: (1R,2R,3R,2’S)Source of chirality: d-glyceraldehyde

(3R,4R,5R)-5-(Hydroxymethyl)piperidine-3,4-diolC6H13NO3[α]D21=+17.8 (c 0.13, EtOH)Absolute configuration: (3R,4R,5R)Source of chirality: d-glyceraldehyde

(3R,4R,5R)-5-((S)-1,2-Dihydroxyethyl)piperidine-3,4-diolC7H15NO4[α]D21=-11.5 (c 0.53, MeOH)Absolute configuration: (3R,4R,5R,1′S)Source of chirality: d-glyceraldehyde