Synthesis of 11‐Oxaestrogens  via  Dye‐Sensitized Photo‐oxygenation of a 9,11‐Didehydroestrone Derivative | Zendy

Planas Antoni | Zendy; Sala Nuria | Zendy; Bonet JuanJulio | Zendy

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Synthesis of 11‐Oxaestrogens via Dye‐Sensitized Photo‐oxygenation of a 9,11‐Didehydroestrone Derivative

Author(s) -

Planas Antoni,

Sala Nuria,

Bonet JuanJulio

Publication year - 1989

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19890720412

Subject(s) - chemistry , derivative (finance) , yield (engineering) , oxygenation , ring (chemistry) , estrone , aldehyde , fragmentation (computing) , skeleton (computer programming) , diol , stereochemistry , organic chemistry , catalysis , ecology , biochemistry , materials science , biology , hormone , computer science , financial economics , programming language , economics , metallurgy , operating system

The 3‐methoxy‐1 1‐oxaestrone ( 13 ) has been synthetized from estrone ( 3 ) following an approach that involves the ring‐C fragmentation of the estrogenic skeleton by dye‐sensitized photo‐oxygenation of the properly C(17)‐protected 9,11‐didehydroestrone derivative 6 as the key step. The C(13)‐side‐chain degradation of the 9‐oxo‐9,11‐seco‐aldehyde 7 followed by reduction to the 9β, 12‐diol 10 and further cyclization yields the 11‐oxaestrogenic skeleton. By this procedure, 13 is obtained in 9 steps from 3 with a non‐optimized overall yield of ca. 15%.

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