131121-30-7Relevant articles and documents
Halichondrin B: Synthesis of the C(1)-C(15) subunit
Burke, Steven D.,Jung, Kyung Woon,Lambert, William T.,Phillips, Jeannie R.,Klovning, Jason J.
, p. 4070 - 4087 (2000)
A short and efficient synthesis of the C(1)-C(15) subunit of halichondrin B in its natural configuration is described. The polycyclic caged ketal 3, containing nine asymmetric centers, is prepared in 14 steps from α-D-glucoheptonic acid γ-lactone (7). Key steps in the two similar routes described include EtMgBr-promoted pinacol ring expansions of hydrory mesylates 23 and 34. intramolecular Michael additions of 29 and 37, and a one-pot, HF-induced conversion of 4 to 3 involving in situ silyl ether cleavage, acetal hydrolysis, Michael addition, and caged ketal formation. Alternative protocols for carbinol inversion at C(11), one early and one late in the synthetic sequence, are also described.
Enantioselective synthesis of the excitatory amino acid (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid
Bradley, Daniel M.,Mapitse, Renameditswe,Thomson, Nicholas M.,Hayes, Christopher J.
, p. 7613 - 7617 (2007/10/03)
An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62-69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.
3, 5, and/or 6 substituted analogues of swainsonine processes for their preparation and their use as therapeutic agents
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, (2008/06/13)
The invention relates to novel 3, 5, and/or 6 swainsonine analogues, processes for their preparation and their use as therapeutic agents. The invention also relates to pharmaceutical compositions containing the compounds and their use as therapeutics.