Synthesis of bufalin

George Pettit; Leonard E. Houghton; John C. Knight; Fred Bruschweiler

doi:10.1039/C29700000093

Synthesis of bufalin

George Pettit, Leonard E. Houghton, John C. Knight, Fred Bruschweiler

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A new total synthesis of resibufogenin and bufalin using digitoxigenin, represents the first chemical transformation of a cardenolide to a bufadienolide.

Original language	English (US)
Pages (from-to)	93-94
Number of pages	2
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	2
DOIs	https://doi.org/10.1039/C29700000093
State	Published - 1970

ASJC Scopus subject areas

Molecular Medicine

Access to Document

10.1039/C29700000093

Cite this

@article{1a5f556213b74aeea0056de398f9aeeb,

title = "Synthesis of bufalin",

abstract = "A new total synthesis of resibufogenin and bufalin using digitoxigenin, represents the first chemical transformation of a cardenolide to a bufadienolide.",

author = "George Pettit and Houghton, {Leonard E.} and Knight, {John C.} and Fred Bruschweiler",

note = "Funding Information: Interconversion of certain cardiac aglycones to their otherwise dif%icultly accessible toad poison counterparts now appears practical. This investigation was supported by Public Health Service Research Grants from the National Cancer Institute. We are also grateful to Professor K. Meyer and Dr. Y. Kamano for generous samples of bufalin. M eO (Received, November 13th, 1969; Corn. 1725.) For previous paper, see G. R. Pettit, J. C. Knight, and P. ]Brown, in the press. M. Kotake and K. Kuwada, Sci. Papers Inst. Phys. Chem. Res., Tokyo, 1939,36, 106 [Chem. Abs., 1939,33, 73041. K. Kuwada, J. Chem. SOC.Japan, 1939,60, 335 [Chern. Abs., 1940,34, 10311; H. Wieland, C. Hesse, and R. Hiittel, Annalen, 1936,524, 203; K. Meyer, Helv. Chim. Acta, 1949, 32, 1238. (a) F. Sondheimer,W. McCrae, and W. G. Salmond, J. Amev. Chem. SOC.,1969,91, 1228; (b) U. Stache, K. Radscheit, W. Fritsch, H. Kohl, W. Haede, and H. Ruschig, Tetrahedron Letters, 1969, 3033. G. R. Pettit, T. R. Kasturi, J. C. Knight, and K. Jaeggi, J. Org. Chem., in the press; T. R. Kasturi, G. R. Pettit, and K. A. Jaeggi,Chem. Comm., 1967, 644. N. Danieli, Y. Mazur, and I?. Sondheimer, Tetrahedron, 1966,22, 3189. G. Bach, J. Capitaine, and C. R. Engel, Canad. J. Chem., 1968,46, 733. *G. R. Pettit, D. C. Fessler, K. D. Paull, P. Hofer, and J. C. Knight, Canad. J. Chem., 1969,47, 2511.",

year = "1970",

doi = "10.1039/C29700000093",

language = "English (US)",

pages = "93--94",

journal = "Journal of the Chemical Society D: Chemical Communications",

issn = "0577-6171",

number = "2",

}

TY - JOUR

T1 - Synthesis of bufalin

AU - Pettit, George

AU - Houghton, Leonard E.

AU - Knight, John C.

AU - Bruschweiler, Fred

N1 - Funding Information: Interconversion of certain cardiac aglycones to their otherwise dif%icultly accessible toad poison counterparts now appears practical. This investigation was supported by Public Health Service Research Grants from the National Cancer Institute. We are also grateful to Professor K. Meyer and Dr. Y. Kamano for generous samples of bufalin. M eO (Received, November 13th, 1969; Corn. 1725.) For previous paper, see G. R. Pettit, J. C. Knight, and P. ]Brown, in the press. M. Kotake and K. Kuwada, Sci. Papers Inst. Phys. Chem. Res., Tokyo, 1939,36, 106 [Chem. Abs., 1939,33, 73041. K. Kuwada, J. Chem. SOC.Japan, 1939,60, 335 [Chern. Abs., 1940,34, 10311; H. Wieland, C. Hesse, and R. Hiittel, Annalen, 1936,524, 203; K. Meyer, Helv. Chim. Acta, 1949, 32, 1238. (a) F. Sondheimer,W. McCrae, and W. G. Salmond, J. Amev. Chem. SOC.,1969,91, 1228; (b) U. Stache, K. Radscheit, W. Fritsch, H. Kohl, W. Haede, and H. Ruschig, Tetrahedron Letters, 1969, 3033. G. R. Pettit, T. R. Kasturi, J. C. Knight, and K. Jaeggi, J. Org. Chem., in the press; T. R. Kasturi, G. R. Pettit, and K. A. Jaeggi,Chem. Comm., 1967, 644. N. Danieli, Y. Mazur, and I?. Sondheimer, Tetrahedron, 1966,22, 3189. G. Bach, J. Capitaine, and C. R. Engel, Canad. J. Chem., 1968,46, 733. *G. R. Pettit, D. C. Fessler, K. D. Paull, P. Hofer, and J. C. Knight, Canad. J. Chem., 1969,47, 2511.

PY - 1970

Y1 - 1970

N2 - A new total synthesis of resibufogenin and bufalin using digitoxigenin, represents the first chemical transformation of a cardenolide to a bufadienolide.

AB - A new total synthesis of resibufogenin and bufalin using digitoxigenin, represents the first chemical transformation of a cardenolide to a bufadienolide.

UR - http://www.scopus.com/inward/record.url?scp=31544436524&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=31544436524&partnerID=8YFLogxK

U2 - 10.1039/C29700000093

DO - 10.1039/C29700000093

M3 - Article

AN - SCOPUS:31544436524

SN - 0577-6171

SP - 93

EP - 94

JO - Journal of the Chemical Society D: Chemical Communications

JF - Journal of the Chemical Society D: Chemical Communications

IS - 2

ER -

Synthesis of bufalin

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this