E-resources
Peer reviewed
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Cagide-Fagín, Fernando; Alonso, Ricardo
European Journal of Organic Chemistry, December 2010, Volume: 2010, Issue: 35Book Review, Journal Article
The synthetic power of the recently developed cascade annulations of β‐(hetero)aryl‐α‐nitro‐α,β‐enals with the pyrrolidine‐derived enamine of 2,2‐dimethyl‐1,3‐dioxan‐5‐one is demonstrated by the first convergent route to (±)‐tetrodotoxin. A batch preparation (11 g) of the protected nitrocyclitol 7 and its capability to sustain a convergent formal synthesis of (±)‐tetrodotoxin in only 26 steps illustrate the practicability of the formal 3+3 annulation ofβ‐heteroaryl‐α‐nitro‐α,β‐enals as well as its versatility for the synthesis of natural products containing highly oxygenated cyclohexanes.
