Totalsynthese von (+)-D-Homoöstron-3-methyläther
作者： Jürg Gutzwiller , Werner Meier , Andor Fürst
关键词: Alkylation 、 Ring (chemistry) 、 Stereochemistry 、 Molecule 、 Ether 、 Total synthesis 、 Bromide 、 Chemistry 、 Hydrogen 、 Synthon
摘要: Total Synthesis of (+)-D-Homoestrone 3-methyl ether A novel total synthesis (+)-D-homoestrone ether (21) is described starting from (S)-8a-methyl-3,4,8,8a-tetrahydro-2H, 7H-naphthalene-1,6-dione (1) as a chiral synthon for the rings C and D. The key step involves alkylation derived 3 with m-methoxyphenacyl bromide (4) an AB-building block to give dioxo-secosteroid 5. Hydrogenation 5 affords trans-decalone 11. As by-products epimeric cis-decalones 12 13 were characterized. Cyclization 11 leads under kinetic control predominantly Δ9(11)-tetraene 14. Catalytic hydrogenation 14 subsequent modification in ring D title compound 21. It was found that also Δ8-isomer 15a add hydrogen α-face molecule extent about 80%. 8α-D-homoestrone derivatives 20a 23 well 9β-isomers 19a 22
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