Studies on the relative reactivity of three hydroxyl groups in aconitine

Journal of Asian Natural Products Research
Xue-Ke SheFeng-Peng Wang

Abstract

The relative reactivity of three hydroxyl groups in aconitine toward acetylation, chlorination, sulfonylation, and oxidation has been studied in this paper. The reduction of C-3 ketone and C-15 ketone derivatives of aconitine was also investigated. It was found that (1) the relative reactivity of three hydroxyl groups toward acetylation, chlorination, and sulfonylation is 3-OH>13-OH>15-OH; (2) 3-OH is much more reactive than 15-OH toward oxidation; and (3) reduction of the carbonyl group at C-3 with NaBH(4) generated a pair of C-3 epimers, while the reduction products of the carbonyl group at C-15 depend largely on the specific reducing agent and the absolute configuration of 16-OCH(3). When the substrate has 16β-OCH(3), its carbonyl group at C-15 can be reduced with NaBH(4) to yield exclusively the 15α-OH-containing product. Upon replacement of reducing agent NaBH(4) with LiAlH(4), the C-15 carbonyl group can be reduced to yield a pair of C-15 epimers. On the other hand, when the substrate has 16α-OCH(3), C-15 carbonyl group can only be reduced to generate 15α-OH-containing product.

References

Jun 1, 1995·Journal of Natural Products·Y BaiS W Pelletier
May 1, 1997·Journal of Natural Products·B S JoshiS W Pelletier
Jul 24, 2010·The Alkaloids. Chemistry and Biology·Feng-Peng Wang, Qiao-Hong Chen

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Citations

Apr 17, 2021·Natural Products and Bioprospecting·Na ZhangGang Xu

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