144242-25-1Relevant articles and documents
Towards synthesis of calysterols, marine sterols with cyclopropene moiety in the side chain: Synthesis of 26,27-Dinor-23H-isocalysterol
Kurek-Tyrlik, Alicja,Minksztym, Kazimierz,Wicha, Jerzy
, p. 1575 - 1588 (2007/10/03)
26,27-Dinor-23H-isocalysterol 24 has been synthesized in 19% yield (6 steps) from ethyl 6β-methoxy-3α,5-cyclo-5α-pregnan-21-oate (18). For construction of the side chain, alkylation of lithium salt of ester 18 with 1-bromo-1,2-dimethyl-c-3-iodomethyl-c-2-(trimethylsilyl)cyclopropane 16 was used. It has been shown that reduction of the ester group in position 21 and rearrangement of the 3,5-cyclosteroid system are compatible with the sidechain functionalities. It has been found that methylation of 1,1-dibromo-2-(trimethylsilyl)cyclopropane is accompanied by an rearrangement involving 1,2-migration of the trimethylsilyl group.