Synthesis of phorbol C-ring analogs: a biomimetic model study on the phorbol to 12-hydroxydaphnetoxin conversion

Autor:	R. C. Desai, Philip L. Fuchs, Sharad S. Magar
Rok vydání:	1992
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone chemistry Bicyclic molecule Stereochemistry Organic Chemistry Phorbol Epoxide Orthoester Cleavage (embryo) Enone Cyclopropane
Zdroj:	The Journal of Organic Chemistry. 57:5360-5369
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00046a017
Popis:	An eight-step synthesis of phorbol C-ring analogs is described. The results of a model study on the phorbol to 12-hydroxy daphnetoxin biomimetic conversion using a C-9 ester-assisted cyclopropyl carbinyl rearrangement are presented. Under the basic conditions used, the dominant reaction pathway is the participation of the C-13 hydroxyl group leading to cleavage of the wrong cyclopropane bond to generate an enone, rather than the desired orthoester
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8810bb72bd4ce5d6b728f6ef60f5dd3a https://doi.org/10.1021/jo00046a017 Zobrazit plný text záznamu