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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A diastereoselective total synthesis of trans-trikentrin A: a ring contraction approach
Luiz F Silva1, Marcus V Craveiro
1Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil. luizfsjr@iq.usp.br
Abstract:
A new route to obtain the polyalkylated indole (+/-)-trans-trikentrin A was developed. The synthesis of this natural alkaloid features a thallium(III)-mediated ring contraction reaction to obtain the trans-1,3-disubstituted five-membered ring in a diastereoselective manner. Thallium(III) is chemoselective in this rearrangement, reacting with the olefin without oxidation of the indole moiety. Other key transformations are the Bartoli's reaction to construct the heterocyclic ring and a Heck coupling to add the carbons atom that will originate the nonaromatic cycle.
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