| Abstract
| - The novel and stereocontrolled synthesis of (±)-tetrodotoxin from myo-inositol is described. Thekey steps involve the stepwise oxidation of hydroxyl groups to the carbonyl function, followed bythe addition of specific nucleophiles, including the successive spiro α-chloroepoxide formation andits ring-opening with the azide anion, to give the desired branched chain structures (5→6,17→18→19→20 and 23→24→25) with the desired regio- and stereoselectivities in high yields. Thestepwise conversion of the α-azido aldehyde 25 to the δ-lactone 29, followed by reduction of theazide, introduction of a guanidine moiety, aldehyde formation, and deprotection, produced the (±)-tetrodotoxin.
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