Chinese Journal of Applied Chemistry ›› 1993, Vol. 0 ›› Issue (1): 12-15.

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STUDIES ON SYNTHESIS OF A/B RING ANALOGUES OF CASTASTERONE Ⅱ.STEREOSELECTIVE SYNTHESIS OF 2β,3β-DIHYDROXY-6-CHOLESTERONE

Gao Bi1, Wang Zhicai1, Zheng Qihuang1, XU Zhiwen2   

  1. 1. Department of Chemistry, Zhongshan University, 510275 Guangzhou;
    2. Department of Chemistry, Xiamen University, Xiamen
  • Received:1992-03-03 Revised:1992-06-24 Published:1993-02-10 Online:1993-02-10

Abstract: 2β, 3β-Dihydroxy-6-cholesterone, a structural analogue in A/B rings of castasterone was stereoselectively synthesized from cholesterol via nitration, reduction; elimination and oxidation reactions. The key step in the synthesis is the introduction of 2β, 3β-dihydroxy groups by oxidation with I2-AgOAe-H2O.

Key words: 2β, 3β-dihydroxycholesterone, castasterone, A/B ring analogue, I2-AgOAc oxidation, synthesis