142329-96-2Relevant academic research and scientific papers
Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4-desmethoxyepisilvestrol
Adams, Tim E.,Sous, Mariana El,Hawkins, Bill C.,Hirner, Sebastian,Holloway, Georgina,et al.
supporting information; experimental part, p. 1607 - 1616 (2009/07/30)
Total synthesis of the anticancer 1,4-dioxane containing natural products silvestrol (1) and episilvestrol (2) is described by an approach basedon the proposed biosynthesis of these novel compounds. The key steps in cluded an oxidative rearrangement of the protected D-glucose derivative 11 to afford the 1,4-dioxane 12, which could be elaborated to the coupling partner 5 and a photochemical [3 + 2] cycloadditon between the 3-hydroxyflavone 27 and methyl cinnamate followed by base-induced α-ketol rearrangement and reduction to give the cyclopentabenzofuran core 33. The core (-)-6 and 1,4-dioxane fragment 5 were united by a highly stereoselective Mitsunobu coupling with the modified azodicarboxylate DMEAD toafford the axial coupled product 36. Deprotection then gave episilvestr ol (2). Silvestrol (1) was synthesized by a coupling between core (-)-6 and the dioxane 44 followed by deprotection. Compound 1 was also synthesized from episilvestrol (2) by a Mitsunobu inversion. In addition, the analogue 4-desmethoxyepisilvestrol (46) was synthesized via the same route. It was found that 46 and episilvestrol 2 displayed an unexpected concentration-dependent chemical shift variation for the nonexchangeable dioxane protons. Synthetic compounds 1, 2, 38, 46, and 54 were tested against cancer cells lines, and it was found that the stereochemistry of the core was critical for activity. Synthetic analogue 4-desmethoxyepisilvestrol (46) was also active against lung and colon cancer cell lines.
Total synthesis of (-)-episilvestrol and (-)-silvestrol
El Sous, Mariana,Khoo, Mui Ling,Holloway, Georgina,Owen, David,Scammells, Peter J.,Rizzacasa, Mark A.
, p. 7835 - 7838 (2008/09/18)
Sugar and spice... The total synthesis of the rare but potent anticancer natural product (-)-episilvestrol and its 5? epimer (-)-silvestrol was accompushed from D-glucose, naringenin, and methyl cinnamate (see scheme). The key steps of the sequence were inspired by the possible biogenesis of these compounds.
PROCESSES AND INTERMEDIATES
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Page/Page column 56; 57, (2010/02/15)
The present invention relates to synthetic processes for the preparation of compounds bearing a dioxanyl moiety, in particular to compounds bearing a dioxanyl side chain attached to a mono- or polycyclic core moiety, more particularly a cyclopentabenzofuran core moiety. The invention also relates to intermediate compounds used in these processes. Compounds which can be prepared by the process of the invention can be used as candidates for screening for potential therapeutic activity, thus the invention also relates to compounds obtainable or prepared by the methods described above, in particular to those having cytotoxic or cytostatic activity.
A practical synthesis of mannosaminyl-β(1 → 4)-glucosyl-α(1 → 2)-rhamnose, the trisaccharide repeating unit of a Streptococcus pneumoniae capsular polysaccharide
Kaji,Lichtenthaler,Osa,Takahashi,Zen
, p. 2401 - 2408 (2007/10/02)
An efficient chemical synthesis is described for the title trisaccharide repeating unit of the capsular polysaccharide of Streptococcus pneumoniae Type 19F. The key intermediate was a well-accessible indirect β-D-mannosaminyl donor, i.e. 2-(benzoyloxyimin
