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- Title
Synthese von (±)-Diplodialid B und A.
- Authors
Shenvi, Ashokkumar B.; Gerlach, Hans
- Abstract
Synthesis of (±)-Diplodialide B and A Two steroid hydroxylase inhibitors, diplodialide B (1) and A (2) have been synthesized in the following way: The lithium enolate 5 of S-t-butyl thioacetate (4) was added to (E)-7-(2′-tetrahydropyranoxy)-2-octen-1-al (8) and the newly formed 3-hydroxy group in the product 9 was protected as t-butyl-diphenyl silyl ether followed by selective hydrolysis of the tetrahydropyranyl ether to give 10. Treatment with AgNO3/H2O cleaved the S-t-butyl ester group in 10 to give the corresponding hydroxy carboxylic acid which was converted into the S-2-pyridyl thioester by treatment with di(2-pyridyl)disulfide and triphenyl phosphine and cyclized with AgClO4 to give the (4 E,3,9- trans)- and (4 E,3,9- cis)-lactone 11 and 12 (R t-Bu(C6H5)2Si) in 67% yield. Chromatographic separation of 11 and 12 and cleavage of the t-butyl-diphenyl silyl ether with tetrabutyl ammonium fluoride yielded (±)-diplodialide B (1) with (4 E,3,9- trans)-configuration and the (4 E,3,9- cis)-isomer 12 (RH). Both isomers could be oxidized to diplodialide A (2) with manganese dioxide. The synthesis described above has also been carried out via the intermediates 10, 11 and 12 with RCOOCH2CH2Si(CH3)3.
- Publication
Helvetica Chimica Acta, 1980, Vol 63, Issue 8, p2426
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19800630835