Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-ox abicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.


Published in:
Tetrahedron-Asymmetry, 8, 20, 3497-3501
Year:
1997
ISSN:
0957-4166
Keywords:
Note:
Univ lausanne,chim sect,bch,ch-1015 lausanne,switzerland.
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


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