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Issue 18, 2019
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Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate

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Abstract

The stereoselective synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E, from a common synthetic intermediate, is disclosed. The propargylic sulfide stereocenter is created stereoselectively via carbon–carbon bond formation in the reaction of α-chloro sulfides with alkynylzinc reagents via 1,2-asymmetric induction by a β-siloxy group. The characteristic 1,4-diol motif of the natural products is introduced by a [2,3] sigmatropic rearrangement of an allylic sulfoxide or by the Mislow–Evans–Braverman rearrangement of a propargylic sulfoxide followed by stereoselective reduction of the ensuing α,β-unsaturated ketone. Unlike earlier reports, the C11/C9 carbinol center is created with excellent stereocontrol and derivatives of natural products differing at C14/C12 can be readily obtained. Catalytic asymmetric protocols and substrate-controlled asymmetric induction are utilized for the efficient introduction of the stereogenic centers.

Graphical abstract: Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate

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Publication details

The article was received on 16 Mar 2019, accepted on 05 Apr 2019 and first published on 08 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00623K
Org. Biomol. Chem., 2019,17, 4572-4592

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    Synthesis of solandelactone F, constanolactone A and an advanced intermediate towards solandelactone E from a common synthetic intermediate

    R. Yalla and S. Raghavan, Org. Biomol. Chem., 2019, 17, 4572
    DOI: 10.1039/C9OB00623K

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