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Synthetic approaches to phomactins: Novel oxidation of homoallylic alcohols using tetra-n-propylammonium perruthenate

Lookup NU author(s): Dr Tim Blackburn

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Abstract

© 2018 Elsevier Ltd Previous studies of a synthesis of phomactin A had resulted in the synthesis of a 15-methylenebicyclo[9.3.1]pentadecadiene. The next step in the synthesis was to be the epoxidation of this methylenecyclohexane that was hoped would lead to a 1-(hydroxymethyl)cyclohexene by rearrangement of the exocyclic epoxide, but the epoxidation was difficult to carry out regioselectively on advanced intermediates. However, oxidation of a 15-methylenebicyclo[9.3.1]pentadeca-3,7-dien-14-ol using tetra-n-propylammonium perruthenate and N-methylmorpholine-N-oxide led to conversion of this homoallylic alcohol into the corresponding 14-oxobicyclo[9.3.1]pentadeca-1(15),3,7-triene-15-carboxaldehyde in one step. Reduction of this using DIBAL-H gave a promising intermediate for a synthesis of a phomactin. The scope of this oxidation of homoallylic alcohols was briefly investigated.

Publication metadata

Author(s): Blackburn TJ, Thomas EJ

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2018

Volume: 74

Issue: 38

Pages: 5399-5407

Print publication date: 20/09/2018

Online publication date: 24/05/2018

Acceptance date: 23/05/2018

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Elsevier Ltd

URL: https://doi.org/10.1016/j.tet.2018.05.068

DOI: 10.1016/j.tet.2018.05.068

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