Synthesis of a Chiral Helical Molecular Template Based on trans-5,6,6a,7,8,12b-Hexahydro-1,12-dimethylbenzo[c]phenanthrene- 5,8-dione

Autor:	Sever Sternhell, Leslie D. Field, Julie Cheung, Trevor W. Hambley
Rok vydání:	1997
Předmět:	chemistry.chemical_compound Template Stereochemistry Chemistry Organic Chemistry ALUMINUM HYDRIDE Absolute configuration chemistry.chemical_element Lithium Template based Phenanthrene
Zdroj:	The Journal of Organic Chemistry. 62:62-66
ISSN:	1520-6904 0022-3263
Popis:	Reduction of trans-5,5,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-dione (1, R(1) = R(4) = H, R(2) = R(3) = CH(3)) with lithium aluminum hydride yielded stereoselectively (5RS,8RS)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diols 2, X = H. These diols proved to be configurationally stable chiral molecular templates capable of straightforward modification by attachment of molecular elements of different length and kind. The structures of the diacetate 2, X = COCH(3), and (5R,8R)-(-)-trans-5,6,6a,7,8,12b-hexahydro-1,12-dimethylbenzo[c]phenanthrene-5,8-diyl di-p-bromobenzoate (2a, X = p-BrC(6)H(4)CO), as well as the absolute configuration of the latter were obtained by X-ray crystallography.
Databáze:	OpenAIRE
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