Structure and stereochemistry of the monobromotigogenins

J. P. Kutney; W. Cretney; G. R. Pettit; J. C. Knight

doi:10.1016/S0040-4020(01)98471-6

Structure and stereochemistry of the monobromotigogenins

J. P. Kutney, W. Cretney, G. R. Pettit, J. C. Knight

Research output: Contribution to journal › Article

6 Scopus citations

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
DOIs	https://doi.org/10.1016/S0040-4020(01)98471-6
State	Published - 1964
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(01)98471-6

Fingerprint Dive into the research topics of 'Structure and stereochemistry of the monobromotigogenins'. Together they form a unique fingerprint.

Cite this

Kutney, J. P., Cretney, W., Pettit, G. R., & Knight, J. C. (1964). Structure and stereochemistry of the monobromotigogenins. Tetrahedron, 20(9), 1999-2006. https://doi.org/10.1016/S0040-4020(01)98471-6

@article{dd2d938d96bc4277ab880d958e5c41f5,

title = "Structure and stereochemistry of the monobromotigogenins",

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.",

author = "Kutney, {J. P.} and W. Cretney and Pettit, {G. R.} and Knight, {J. C.}",

year = "1964",

doi = "10.1016/S0040-4020(01)98471-6",

language = "English (US)",

volume = "20",

pages = "1999--2006",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "9",

}

TY - JOUR

T1 - Structure and stereochemistry of the monobromotigogenins

AU - Kutney, J. P.

AU - Cretney, W.

AU - Pettit, G. R.

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

U2 - 10.1016/S0040-4020(01)98471-6

DO - 10.1016/S0040-4020(01)98471-6

M3 - Article

AN - SCOPUS:50549221451

VL - 20

SP - 1999

EP - 2006

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 9

ER -