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Sea the synthesis: At ambient temperature, tert-butyllithium promotes a Barbier-type macrocyclization in the first total synthesis of (−)-gymnodimine (Ts: toluene-4-sulfonyl; TBS: tert-butyldimethylsilyl), a member of the spirocyclic-imine family of marine toxins. The synthesis also features a vinylogous Mukaiyama aldol process to couple the labile butenolide moiety onto a macrocyclic ketone intermediate.
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Kong et al. (2009) studied this question.
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