Bufadienolides. 5. Synthesis of Cardenolides

George Pettit; Cherry L. Herald; John P. Yardley

doi:10.1021/jo00830a029

Bufadienolides. 5. Synthesis of Cardenolides

George Pettit, Cherry L. Herald, John P. Yardley

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Abstract

Boron trifluoride catalyzed lead tetraacetate oxidation of 30-acetoxy-2O-oxo-oa-pregnane and of pregnenolone acetate was employed to obtain the corresponding 21-acetoxy derivatives. Reaction of 3β,21-diacetoxy-20-oxo-5a-pregnane (1) with the anion prepared from diethyl cyanomethylphosphonate and subsequent treatment with hydrochloric acid afforded the corresponding nitrile (2) and derived imino lactone hydrochloride (3a). Acid hydrolysis of the imino lactone gave 3β-acetoxy-5<x-cardenolide (4b). Analogous transformation of ketone 6 provided 3β-acetoxy-A6-cardenolide (10b). The two-step reaction sequence from readily available a-hydroxy ketones provides a potentially useful route to imino lactones and butenolides.

Original language	English (US)
Pages (from-to)	1389-1392
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	35
Issue number	5
DOIs	https://doi.org/10.1021/jo00830a029
State	Published - May 1 1970

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Organic Chemistry

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abstract = "Boron trifluoride catalyzed lead tetraacetate oxidation of 30-acetoxy-2O-oxo-oa-pregnane and of pregnenolone acetate was employed to obtain the corresponding 21-acetoxy derivatives. Reaction of 3β,21-diacetoxy-20-oxo-5a-pregnane (1) with the anion prepared from diethyl cyanomethylphosphonate and subsequent treatment with hydrochloric acid afforded the corresponding nitrile (2) and derived imino lactone hydrochloride (3a). Acid hydrolysis of the imino lactone gave 3β-acetoxy-5",

author = "George Pettit and Herald, {Cherry L.} and Yardley, {John P.}",

year = "1970",

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doi = "10.1021/jo00830a029",

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AU - Pettit, George

AU - Herald, Cherry L.

AU - Yardley, John P.

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N2 - Boron trifluoride catalyzed lead tetraacetate oxidation of 30-acetoxy-2O-oxo-oa-pregnane and of pregnenolone acetate was employed to obtain the corresponding 21-acetoxy derivatives. Reaction of 3β,21-diacetoxy-20-oxo-5a-pregnane (1) with the anion prepared from diethyl cyanomethylphosphonate and subsequent treatment with hydrochloric acid afforded the corresponding nitrile (2) and derived imino lactone hydrochloride (3a). Acid hydrolysis of the imino lactone gave 3β-acetoxy-5

AB - Boron trifluoride catalyzed lead tetraacetate oxidation of 30-acetoxy-2O-oxo-oa-pregnane and of pregnenolone acetate was employed to obtain the corresponding 21-acetoxy derivatives. Reaction of 3β,21-diacetoxy-20-oxo-5a-pregnane (1) with the anion prepared from diethyl cyanomethylphosphonate and subsequent treatment with hydrochloric acid afforded the corresponding nitrile (2) and derived imino lactone hydrochloride (3a). Acid hydrolysis of the imino lactone gave 3β-acetoxy-5

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Bufadienolides. 5. Synthesis of Cardenolides

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