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Cascade reactions

The first enantioselectiv synthesis of (-)-Gilbertine with a cationic cascade reaktion as the key step.

Uleine-type alkaloids have been of synthetic interest over the past decades. Gilbertine was first discovered in 1982 and remained a challenge for synthetic organic chemists for more than 20 years. Gilbertine displays a much more complex structure than uleiene itself as it consists of a pentacyclic skeleton and an additional stereocenter.
Our strategy was based on a cationic cascade reaction of a chiral tetrahydrocarbazole which was synthesized by a convenient Fischer indole synthesis. The stereochemistry was set up by a Shibasaki Michael addition.
In summary the Uleine-type indole alkaloide (-)-Gilbertine has been synthesised starting from cyclohexenone in 17 steps in a 5.5 % overall yield. The key step, a cationic cascade cyclisation forming a tetrahydropyrane and piperidine ring and the pentacyclic framework in one step, was shown to be highly steroselective.

J. Jiricek, S. Blechert, J. Am. Chem. Soc. 2004, 126, 3534-3538. [DOI]

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