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An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone
Departamento de Química, Universidade Federal do Espírito Santo, 29060-900, Vitória, ES, Brazil
Departamento de Química, Universidade Federal de São Carlos, Caixa Postal 676, 13565-905, São Carlos, SP, Brazil
* Author to whom correspondence should be addressed.
Received: 23 May 2001; in revised form: 15 January 2002 / Accepted: 31 January 2002 / Published: 28 February 2002
Abstract: (-)-Carvone (3) has been efficiently transformed into (-)-3β-hydroxycarvone (1), which is expected to be a useful synthon or chiral template in the synthesis of natural molecules. This short and efficient synthesis of compound 1 involves regioselective and stereoselective α-hydroxylation of carvone via the trimethylsilyl-dienyl-ether derivative.
Keywords: Carvone; 3β-hydroxycarvone; silyl enol ether; stereoselective synthesis
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Dos Santos, R.B.; Brocksom, T.J.; Zanotto, P.R.; Brocksom, U. An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone. Molecules 2002, 7, 129-134.
Dos Santos RB, Brocksom TJ, Zanotto PR, Brocksom U. An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone. Molecules. 2002; 7(2):129-134.
Dos Santos, Reginaldo B.; Brocksom, Timothy J.; Zanotto, Paulo R.; Brocksom, Ursula. 2002. "An Improved Three Step Synthesis of (-)-3β-Hydroxycarvone from (-)-Carvone." Molecules 7, no. 2: 129-134.