1984
DOI: 10.1139/v84-054
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Synthetic cardenolides and related products. IV. D-homo derivatives

Abstract: The synthesis of novel structures related to naturally occurring cardiotonic agents such as resibufogenin is described. These products retain the essential features of aglycones needed for biological activity. They are, however, thermodynamically stable and easily available from smilagenin. The methods of preparation, together with the proof of structures and configuration, are reported.

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Cited by 7 publications
(4 citation statements)
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“…As ricciocarpin B ( 2 ) only differs from 1 within the five‐membered ring, we tried to convert 1 into 2 by oxidation (Scheme ). The bislactones 2 and 16 were obtained after [4+2] cycloaddition with singlet oxygen and subsequent thermal decomposition of the primary adduct as well as reduction with sodium borohydride 15, 16. By comparison of the analytical data with literature values1a 2 could be identified as ricciocarpin B 17.…”
Section: Methodsmentioning
confidence: 99%
“…As ricciocarpin B ( 2 ) only differs from 1 within the five‐membered ring, we tried to convert 1 into 2 by oxidation (Scheme ). The bislactones 2 and 16 were obtained after [4+2] cycloaddition with singlet oxygen and subsequent thermal decomposition of the primary adduct as well as reduction with sodium borohydride 15, 16. By comparison of the analytical data with literature values1a 2 could be identified as ricciocarpin B 17.…”
Section: Methodsmentioning
confidence: 99%
“…To our surprise, no conversion was observed upon treatment of 1 with m-chloroperbenzoic acid [21] or peracetic acid. [22] On the other hand, photooxygenation [23] of 1 was successful. After [4 2] cycloaddition with singlet oxygen and subsequent thermal decomposition of the primary adduct as well as reduction with sodium borohydride, a 1:1 mixture of the bislactones 2 and 17 was obtained.…”
Section: Full Papersmentioning
confidence: 99%
“…The bislactones 2 and 16 were obtained after [42] cycloaddition with singlet oxygen and subsequent thermal decomposition of the primary adduct as well as reduction with sodium borohydride. [15,16] By comparison of the analytical data with literature values [1a] 2 could be identified as ricciocarpin B. [17] To the best of our knowledge the transformation of 1 to 2 reported here constitutes the first synthesis of ricciocarpin B.…”
Section: Methodsmentioning
confidence: 79%