Abstract
Bromination of desoxytigogenin has been found to yield two isomeric 23-bromo-5α-25R-spirostans. The corresponding 3β-acetoxy-23-bromo-5α-25R-spirostans were also prepared from tigogenin actetate. A combination of physical methods based on mass spectrometry and NMR measurements, at 60- and 100-mc/s, have been used to confirm attack by bromine at C-23 of the spiroketal system. The configuration of each epimeric pair (at C-23, cf. III and IV) of isomers was also determined.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1999-2006 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 20 |
| Issue number | 9 |
| State | Published - 1964 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Biochemistry
Cite this
Structure and stereochemistry of the monobromotigogenins. / Kutney, J. P.; Cretney, W.; Pettit, George; Knight, J. C.
In: Tetrahedron, Vol. 20, No. 9, 1964, p. 1999-2006.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Structure and stereochemistry of the monobromotigogenins
AU - Kutney, J. P.
AU - Cretney, W.
AU - Pettit, George
AU - Knight, J. C.
PY - 1964
Y1 - 1964
N2 - Bromination of desoxytigogenin has been found to yield two isomeric 23-bromo-5α-25R-spirostans. The corresponding 3β-acetoxy-23-bromo-5α-25R-spirostans were also prepared from tigogenin actetate. A combination of physical methods based on mass spectrometry and NMR measurements, at 60- and 100-mc/s, have been used to confirm attack by bromine at C-23 of the spiroketal system. The configuration of each epimeric pair (at C-23, cf. III and IV) of isomers was also determined.
AB - Bromination of desoxytigogenin has been found to yield two isomeric 23-bromo-5α-25R-spirostans. The corresponding 3β-acetoxy-23-bromo-5α-25R-spirostans were also prepared from tigogenin actetate. A combination of physical methods based on mass spectrometry and NMR measurements, at 60- and 100-mc/s, have been used to confirm attack by bromine at C-23 of the spiroketal system. The configuration of each epimeric pair (at C-23, cf. III and IV) of isomers was also determined.
UR - http://www.scopus.com/inward/record.url?scp=50549221451&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=50549221451&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:50549221451
VL - 20
SP - 1999
EP - 2006
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 9
ER -