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 |
| State | Published - Jan 1 2002 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis of 10b(R)-hydroxypancratistatin, 10b(S)-hydroxy-1-epipancratistatin, 10b(S)-hydroxy-1,2-diepipancratistatin and related isocarbostyrils. / Pettit, George; Melody, Noeleen; Herald, Delbert L.; Schmidt, Jean M.; Pettit, Robin; Chapuis, Jean.
In: Heterocycles, Vol. 56, No. 1-2, 01.01.2002, p. 139-155.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Synthesis of 10b(R)-hydroxypancratistatin, 10b(S)-hydroxy-1-epipancratistatin, 10b(S)-hydroxy-1,2-diepipancratistatin and related isocarbostyrils
AU - Pettit, George
AU - Melody, Noeleen
AU - Herald, Delbert L.
AU - Schmidt, Jean M.
AU - Pettit, Robin
AU - Chapuis, Jean
PY - 2002/1/1
Y1 - 2002/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0036148244&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036148244&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0036148244
VL - 56
SP - 139
EP - 155
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1-2
ER -