Abstract
Narciclasine (2) was transformed by a series of reactions where Sharpless asymmetric hydroxylations served as the stereochemical controlling step to 10b(R)-hydroxypancratistatin (3), 10b(S)-hydroxy-1-epipancratistatin (13) and 10b(S)-hydroxy-1,2-diepipancratistatin (16). Synthesis of 10b(S)-hydroxy-1,2-diepipancratistatin (16) proceeded from α-triol (11) via cyclic sulfate (14) and inversion of C-2 with cesium benzoate followed by saponification and treatment with a catalytic amount of acid. Compared to pancratistatin (1), these structural modifications led to decreased cancer cell growth inhibition against a minipanel of human cancer cell lines. Narciclasine (2) inhibited the pathogenic yeast Cryptococcus neoformans, and modifications (4, 14 and 15) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae.
Original language | English (US) |
---|---|
Pages (from-to) | 139-155 |
Number of pages | 17 |
Journal | Heterocycles |
Volume | 56 |
Issue number | 1-2 |
DOIs | |
State | Published - Jan 1 2002 |
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
Fingerprint
Dive into the research topics of 'Synthesis of 10b(R)-hydroxypancratistatin, 10b(S)-hydroxy-1-epipancratistatin, 10b(S)-hydroxy-1,2-diepipancratistatin and related isocarbostyrils'. Together they form a unique fingerprint.Datasets
-
CCDC 183152: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Herald, D. L. (Creator), Schmidt, J. M. (Creator), Pettit, R. K. (Creator) & Chapuis, J. (Creator), The Cambridge Structural Database, 2002
DOI: 10.5517/cc64l41, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc64l41&sid=DataCite
Dataset
-
CCDC 183151: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Melody, N. (Creator), Herald, D. L. (Creator), Schmidt, J. M. (Creator), Pettit, R. K. (Creator) & Chapuis, J. (Creator), The Cambridge Structural Database, 2002
DOI: 10.5517/cc64l30, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc64l30&sid=DataCite
Dataset