| Literature DB >> 16354099 |
Peter J L M Quaedflieg1, Bart R R Kesteleyn, Piet B T P Wigerinck, Nicolaas M F Goyvaerts, Robert Jan Vijn, Constantinus S M Liebregts, Jaap H M H Kooistra, Claudia Cusan.
Abstract
[reaction: see text] Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.Entities:
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Year: 2005 PMID： 16354099 DOI： 10.1021/ol052554i
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005