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1.
Complete structure of the mycolactones.
Fidanze, S; Song, F; Szlosek-Pinaud, M; Small, P L; Kishi, Y.
J Am Chem Soc ; 123(41): 10117-8, 2001 Oct 17.
Article in English | MEDLINE | ID: mdl-11592899

Subject(s)
Bacterial Toxins/chemistry , Bacterial Toxins/isolation & purification , Kinetics , Macrolides , Mycobacterium ulcerans/chemistry , Nuclear Magnetic Resonance, Biomolecular , Stereoisomerism
2.
Stereochemistry of the core structure of the mycolactones.
Benowitz, A B; Fidanze, S; Small, P L; Kishi, Y.
J Am Chem Soc ; 123(21): 5128-9, 2001 May 30.
Article in English | MEDLINE | ID: mdl-11457356

Subject(s)
Bacterial Toxins/chemistry , Macrolides , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Stereoisomerism
3.
Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy.
Ghosh, A K; Fidanze, S.
Org Lett ; 2(16): 2405-7, 2000 Aug 10.
Article in English | MEDLINE | ID: mdl-10956507

ABSTRACT

A stereoselective synthesis of (-)-tetrahydrolipstatin is described. The synthesis involves an asymmetric ester derived titanium enolate anti-aldol reaction, a nitro-aldol reaction to append the C-2' C(11) side chain, and a diastereoselective reduction of a beta-hydroxy ketone to an anti-1,3-diol functionality followed by its elaboration to (-)-tetrahydrolipstatin.


Subject(s)
Enzyme Inhibitors/chemical synthesis , Lactones/chemical synthesis , Enzyme Inhibitors/chemistry , Indicators and Reagents , Lactones/chemistry , Models, Molecular , Molecular Conformation , Orlistat , Streptomyces
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