Polyketide library synthesis: Conformational control in extended polypropionates

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7445-7448

  Paterson, Ian ^a   Scott, Jeremy P ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

POLYKETIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030768739     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01752-8     Document Type: Article

References (13)

1. Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 38, 7441.
2. For a review on conformational aspects of polypropionates, see: Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124.
3. For leading references to other work on conformationally restricted, acyclic systems, see: (a) Göttlich, R.; Kahrs, B. C.; Krüger, J.; Hoffmann, R. W. Chem. Commun. 1997, 247.
4. (b) Hoffmann, R. W.; Schopfer, U.; Stahl, M. Tetrahedron Lett. 1997, 38, 4055.
5. (c) Göttlich, R.; Fäcke, T.; Rolle, U.; Hoffmann, R. W. J. Chem. Soc., Perkin Trans. II 1996, 2059.
6. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
7. 7 [M+1] requires 499.3635.
8. (a) Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
9. (b) Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; de Leeuw, H. P. M.; Altona, C. Org. Magn. Reson. 1981, 15, 43.
10. The local conformation trans-trans leads to a straight main chain, with idealised dihedral angles of 180°, as shown in Fig 5. chemical equations presented
11. -1 of the global minimum, all of which had essentially an identical main chain conformation, differing only in the orientations of the unconstrained ethyl and benzyloxy termini.
12. 1 methylene protons.
13. 3OD, precluding direct comparison with the studies on 1.