Synthesis 2003(12): 1827-1836
DOI: 10.1055/s-2003-41025
PAPER
© Georg ThiemeVerlag Stuttgart · New York

Stereoselective Synthesis ofEnantiomerically Pure, Orthogonally Protected 2-Methylenecyclohexane-1,3,5-triolsand 2,4,6-Trihydroxycyclohexanones

Stefan Kirsch, Thorsten Bach*
Lehrstuhl für Organische ChemieI, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315.; e-Mail: thorsten.bach@ch.tum.de;
Weitere Informationen

Publikationsverlauf

Received 4 July 2003
Publikationsdatum:
13. August 2003 (online)

Abstract

The triply silyl protected 2-methylenecyclohexane-1,3,5-triols 1a-c (C-1: tert-butyldimethylsilyl, TBDMS; C-3:tri­methylsilyl, TMS; C-5: tert-butyldiphenylsilyl,TBDPS) were prepared from (R)-(-)-carvonein seven synthetic steps (overall yields: 29-53%).Ozonolysis in the presence of triethylamine yielded the triply protected2,4,6-trihydroxycyclohexanones 2a-c (85%-quant.). The configurationof the products was proven by NOESY studies and by chemical correlation.

5

Synthesis of Wailupemycin B: Kirsch,S.; Bach, T. Angew. Chem. Int. Ed. 2003, 42, inprint.