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 › peer-review

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

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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",

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pages = "1999--2006",

journal = "Tetrahedron",

issn = "0040-4020",

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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.

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

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AN - SCOPUS:50549221451

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EP - 2006

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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