Abstract
By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 417-422 |
| Number of pages | 6 |
| Journal | Journal of Natural Products |
| Volume | 70 |
| Issue number | 3 |
| DOIs | |
| State | Published - Mar 2007 |
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ASJC Scopus subject areas
- Plant Science
- Chemistry (miscellaneous)
- Drug Discovery
- Organic Chemistry
- Pharmacology
Cite this
Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine. / Pettit, George; Melody, Noeleen; Herald, Delbert L.; Knight, John C.; Chapuis, Jean.
In: Journal of Natural Products, Vol. 70, No. 3, 03.2007, p. 417-422.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine
AU - Pettit, George
AU - Melody, Noeleen
AU - Herald, Delbert L.
AU - Knight, John C.
AU - Chapuis, Jean
PY - 2007/3
Y1 - 2007/3
N2 - By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.
AB - By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.
UR - http://www.scopus.com/inward/record.url?scp=34247169948&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34247169948&partnerID=8YFLogxK
U2 - 10.1021/np068046e
DO - 10.1021/np068046e
M3 - Article
VL - 70
SP - 417
EP - 422
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 3
ER -