Synthetic approach to analogues of the original structure of sclerophytin A.
A route to analogues of the original structure of sclerophytin A is described. The beta-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
Pontillo
Joseph
J
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D001952:Bridged-Ring Compounds; D005663:Furans; D011714:Pyrans; C412667:sclerophytin A