Chemoselective reactioms of 14,17α-bis(hydroxymethyl)-3-methoxyestra-1,3,5(10)-trien-17β-ol. Synthesis of novel 14,17-hetero-bridged 19-norsteroids

Add time:07/24/2019    Source:sciencedirect.com

Chemoselective differentiation of the primary hydroxy groups in 14,17α-bis(hydroxymethyl)-3-methoxyestra-1,3,5(10)-trien-17β-ol (2) has been investigated in a series of reactions which lead inter alia to novel 14,17-hetero-bridged steroid hormone analogues. Thus routes are described to 3-methoxy-14,17α-(2-oxapropano)estra-1,3,5(10)-trien-17β-ol (4) and 17α 14-epoxymethano-17β-hydroxymethyl-3-methoxyestra-1,3,5(10)-triene (8). Related experiments show that the 171-hydroxy group in (2) is preferentially functionalised and that 171-tosyloxy 141-ethers undergo facile intramolecular participation reactions. The utility of certain intermediates in the synthesis of hormone analogues is exemplified by conversion of (8) into 17α,14-epoxymethano-19-norpregn-4-ene-3,20-dione (36).

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