Synthesis of Naturally Occurring Diosphenols and Hydroxydiosphenols

Viljoen, Murray S.

doi:10.1081/scc-120003623

Cited by 7 publications

(1 citation statement)

References 9 publications

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“…Literature precedent with regard to diosphenols is, for our purposes, rich yet somewhat lacking. A significant number of their syntheses have made their appearance, but many begin from the corresponding α-hydroxy ketone, α,β-epoxy ketone, α,α-dibromo ketone, or other functionalized substrate not applicable here . Presently, it was mandatory for reasons of reaction economy that 2 be the immediate precursor of 4 .…”

Section: Resultsmentioning

confidence: 99%

Diosphenol-Based Approach to the A-Ring Functionalization of Advanced Taxol Precursors

Kreilein¹,

Hofferberth²,

Hart³

et al. 2006

J. Org. Chem.

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Several different approaches to the A-ring functionalization of an advanced, highly functionalized diosphenol precursor to Taxol are described. The first phase of the undertaking consists of an assessment of those reagents conducive to reaction at the enolic oxygen (silylation, methylation, allylation, and acylation). Transformations involving an alternative attack at the enol carbon center (bromination, selenation) have also been defined. Sodium borohydride reduction operates from the beta-face of C-14 as long as the C-1 hydroxyl is not protected so as to offer steric exclusion. Complications associated with various aspects of these methodological undertakings are addressed. The most advanced oxygenation achievements were realized by way of a noteworthy sequence involving epoxidation of the O-methyl ether, methanolysis under mildly acidic conditions, and regioselective oxidation of diol 38 to give 39.

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Section: Resultsmentioning

confidence: 99%

Diosphenol-Based Approach to the A-Ring Functionalization of Advanced Taxol Precursors

Kreilein¹,

Hofferberth²,

Hart³

et al. 2006

J. Org. Chem.

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Synthesis of Naturally Occurring Diosphenols and Hydroxydiosphenols.

Viljoen

2002

ChemInform

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Biotransformation and molecular docking studies of aromatase inhibitors

et al. 2016

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Bioconversion of the aromatase inhibitor formestane (4-hydroxyandrost-4-ene-3,17-dione) (1) by the fungus Rhizopus oryzae ATCC 11145 resulted in a new minor metabolite 3,5α-dihydroxyandrost-2-ene-4,17-dione (2) and the known 4β,5α-dihydroxyandrostane-4,17-dione (3) as the major product. The structural elucidation and bioactivities of these metabolites are reported herein. Molecular modeling studies of the interactions between these metabolites and the aromatase protein indicated that acidic (D309), basic (R115), polar (T310), aromatic (F134, F221, and W224), and non-polar (I133, I305, A306, V369, V370, L372, V373, M374, and L477) amino acid residues contribute important interactions with the steroidal substrates. These combined experimental and theoretical studies provide fresh insights for the further development of more potent aromatase inhibitors.

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Synthesis of Naturally Occurring Diosphenols and Hydroxydiosphenols

Cited by 7 publications

References 9 publications

Diosphenol-Based Approach to the A-Ring Functionalization of Advanced Taxol Precursors

Diosphenol-Based Approach to the A-Ring Functionalization of Advanced Taxol Precursors

Synthesis of Naturally Occurring Diosphenols and Hydroxydiosphenols.

Biotransformation and molecular docking studies of aromatase inhibitors

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