Peer-Reviewed Journal Details
Mandatory Fields
Burnell, ES;Irshad, AR;Raftery, J;Thomas, EJ
2015
June
Tetrahedron Letters
Approaches to phomactin A: unexpected late-stage observations
Published
WOS: 1 ()
Optional Fields
TETRAPROPYLAMMONIUM PERRUTHENATE TRICYCLIC FURANOCHROMAN MAGNESIUM BROMIDE ALCOHOLS MILD REARRANGEMENTS ANTAGONIST PRECURSORS OXIDANT CORE
56
3255
3258
A dihydroxyepoxide analogous to that proposed as a late intermediate in the biosynthesis of phomactin A was prepared by reduction of the corresponding ketoaldehyde. The structure of the dihydroxyepoxide, specifically its configuration at C14, was confirmed by the X-ray crystal structure of its diacetate. The stereoselectivity of reduction of the ketoaldehyde would appear to be influenced by the presence of a remote phenylsulphonyl moiety at C10. Of interest in the context of the biosynthesis of phomactin A was the observation that this dihydroxyepoxide did not rearrange into the isomeric hydroxytetrahydropyran despite having the configuration at C14 required for this rearrangement. (C) 2015 Elsevier Ltd. All rights reserved.
0040-4039
10.1016/j.tetlet.2015.01.082
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