A Diastereoselective Total Synthesis of trans-Trikentrin A: A Ring Contraction Approach


Autoria(s): SILVA JR., Luiz F.; CRAVEIRO, Marcus V.
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

20/10/2012

20/10/2012

2008

Resumo

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.

Identificador

ORGANIC LETTERS, v.10, n.23, p.5417-5420, 2008

1523-7060

http://producao.usp.br/handle/BDPI/31542

10.1021/ol8023105

http://dx.doi.org/10.1021/ol8023105

Idioma(s)

eng

Publicador

AMER CHEMICAL SOC

Relação

Organic Letters

Direitos

restrictedAccess

Copyright AMER CHEMICAL SOC

Palavras-Chave #ENANTIOSELECTIVE TOTAL-SYNTHESIS #ABSOLUTE STRUCTURES #NATURAL HERBINDOLES #THALLIUM(III) SALTS #(+/-)-CIS-TRIKENTRIN-A #INDOLES #REAGENTS #(6R,8R)-ISO-TRANS-TRIKENTRIN-B #(+/-)-ISO-TRANS-TRIKENTRIN-B #(6R,8R)-TRANS-TRIKENTRIN-B #Chemistry, Organic
Tipo

article

original article

publishedVersion