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The total synthesis of membrarollin

The total synthesis of membrarollin
The total synthesis of membrarollin

A model adjacent bis-THF compound has been prepared with the installation of the first THF ring by a chiral auxiliary directed oxidative cyclisation of 1,5,9-dienyne 4.24 by potassium permanganate. The second THF ring was introduced by an acyl perrhenate cyclisation of hydroxyl-alkene 4.28. A crystal structure of the adjacent bis-THF product was obtained which showed the unexpected trans ring formed in the second cyclisation.

The central adjacent bis-THF core of the Annonaceous acetogenin membrarollin was established via a permanganate promoted selective oxidative cyclisation of 1,5,9-triene 5.26 followed by a base-induced cyclisation of cyclic sulphate 5.35. Elaboration of the central core to terminal alkene 5.39 allowed the introduction of the butenolide fragment by Trost’s ruthenium catalysed Alder-ene reaction. Selective alkene reduction completed the synthesis of membrarollin.

University of Southampton
Kay, Claire-Louise
e656f352-aed5-4a27-bece-8d19722a9e83
Kay, Claire-Louise
e656f352-aed5-4a27-bece-8d19722a9e83

Kay, Claire-Louise (2006) The total synthesis of membrarollin. University of Southampton, Doctoral Thesis.

Record type: Thesis (Doctoral)

Abstract

A model adjacent bis-THF compound has been prepared with the installation of the first THF ring by a chiral auxiliary directed oxidative cyclisation of 1,5,9-dienyne 4.24 by potassium permanganate. The second THF ring was introduced by an acyl perrhenate cyclisation of hydroxyl-alkene 4.28. A crystal structure of the adjacent bis-THF product was obtained which showed the unexpected trans ring formed in the second cyclisation.

The central adjacent bis-THF core of the Annonaceous acetogenin membrarollin was established via a permanganate promoted selective oxidative cyclisation of 1,5,9-triene 5.26 followed by a base-induced cyclisation of cyclic sulphate 5.35. Elaboration of the central core to terminal alkene 5.39 allowed the introduction of the butenolide fragment by Trost’s ruthenium catalysed Alder-ene reaction. Selective alkene reduction completed the synthesis of membrarollin.

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Published date: 2006

Identifiers

Local EPrints ID: 466186
URI: http://eprints.soton.ac.uk/id/eprint/466186
PURE UUID: ea04e0ed-d884-49b8-a751-bbcd1b8ad150

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Date deposited: 05 Jul 2022 04:41
Last modified: 16 Mar 2024 20:33

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Contributors

Author: Claire-Louise Kay

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