论文信息 - Stereoselective synthesis of C/D/E rings in steroids containing E (lactone) ring. Synthesis of (±)-1-(1'-hydroxyethyl)-7,7a-dihydro-5(6H)-indanone-7a-carboxylic acid-7a,1'-lactone

Stereoselective synthesis of C/D/E rings in steroids containing E (lactone) ring. Synthesis of (±)-1-(1'-hydroxyethyl)-7,7a-dihydro-5(6H)-indanone-7a-carboxylic acid-7a,1'-lactone

The title compound, a potential intermediate for the synthesis of steroids containing E (lactone) ring, was synthesized stereoselectively using the acid catalyzed homoconjugate addition of methanol to methyl 6-methyl-2-oxobicyclo[3.1.0]hexane-1-carboxylate in four steps.

M. Nakayama | S. Tanimori | M. Hashio | Y. Mitani

[1] T. Hiyama,et al. Bis(trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-Carbon , 1984 .

[2] J. Howbert,et al. Synthetic studies on arene-olefin cycloadditions -III- total synthesis of (±)-hirsutene☆ , 1982 .

[3] James D White,et al. Spiroannelation via intramolecular ketocarbenoid addition. Stereocontrolled synthesis of (-)-acorenone B and (.+-.)-.alpha.-chamigrene , 1981 .

[4] P. Crabbé,et al. Stereochemistry of the alkaloid gitingensine. , 1967, The Journal of organic chemistry.

[5] P. Wieland,et al. Partialsynthese von Aldosteron. Über Steroide, 177. Mitteilung , 1961 .