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Issue 69, 2018, Issue in Progress
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Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C

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Abstract

The stereochemical outcome of the epoxidation of Δ14–15 cholestanes with mCPBA is controlled by the steric bulk of a C17 substituent. When the C17 is in the β configuration, the epoxide is formed in the α face, whereas if the C17 is trigonal (flat) or the substituent is in the α configuration, the epoxide is formed in the β face. The presence of a hydroxyl substituent at C20 does not influence the stereochemical outcome of the epoxidation.

Graphical abstract: Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C

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Publication details

The article was received on 15 Oct 2018, accepted on 16 Nov 2018 and first published on 27 Nov 2018


Article type: Paper
DOI: 10.1039/C8RA08540D
Citation: RSC Adv., 2018,8, 39691-39695
  • Open access: Creative Commons BY-NC license
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    Control of the stereochemistry of C14 hydroxyl during the total synthesis of withanolide E and physachenolide C

    M. Anees, S. Nayak, K. Afarinkia and V. Vinader, RSC Adv., 2018, 8, 39691
    DOI: 10.1039/C8RA08540D

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