Browse by author
Lookup NU author(s): Dr Tim Blackburn
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
© 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.
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
Altmetrics provided by Altmetric