Combining the [2,3] sigmatropic rearrangement and ring-closing metathesis strategies for the synthesis of spirocyclic alkaloids. A short and efficient route to (+/-)-perhydrohistrionicotoxin.

• This paper describes the use of selenium-based [2,3] sigmatropic rearrangement in combination with ruthenium-catalyzed ring-closing metathesis (RCM) for the synthesis of azaspiro ring systems, as exemplified by the reactions of model substrates 5 and 6.

Nyckelord

rearrangements; metathesis; spiro compounds; alkaloids; MOLECULAR-FORCE FIELD; N-PHENYLSELENOPHTHALIMIDE; ORGANIC-SYNTHESIS; PHENYL SELENIDES; EPOTHILONE-A; MMFF94; GEOMETRIES; CATALYSTS; COMPONENT; ALCOHOLS

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