Swainsonine → Hexahydro-1H-pyrrolizine-1,2,6,7-tetraol

Reaction equation

[CH2:1]1[CH2:9][N:8]2[C@@H:4]([C@H:5]([OH:11])[C@H:6]([OH:10])[CH2:7]2)[C@H:3]([OH:12])C1.C1(=O)O[C@@H]([C@@H]([C@@H](CO)O)O)[C@H](O)[C@@H]1[OH:15]>>[OH:12][CH:3]1[CH:4]2[N:8]([CH2:7][CH:6]([OH:10])[CH:5]2[OH:11])[CH2:9][CH:1]1[OH:15]

Participants

Reactant 2

HCID 51683Swainsonine

HCID 95162420d-Glycero-d-talo-heptono-1,4-lactone

Product 1

HCID 14683616Hexahydro-1H-pyrrolizine-1,2,6,7-tetraol

Procedure

The tetrahydroxypyrrolizidone (1) is an analogue of 1,8-diepiswainsonine. A similar analogue of swainsonine can be made by analogous methods starting with D-glycero-D-talo-heptono-1,4-lactone to produce the novel (1S), 2R, 6R, 7S)-1,2,6,7-tetrahydroxypyrrolizidine.

Sources & evidence

ORD record: ord-af2dc18516984b5cb0d9ec46a058d3a1
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05025098

Reaction notes

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