Abstract
Bicyclic dibrominated C15 medium-ring ether hexahydrolaureoxanyne was produced directly from an acyclic model C15-epoxide when treated with NBS with water as the solvent.
Highlights
Proof-of-principle direct double cyclisation of a linear C15-precursor to a dibrominated bicyclic medium-ring ether relevant to Laurencia species†
Various recent studies have been directed at the further understanding of their biogenesis,[6] where the early pioneering work of Murai[7] demonstrated enzymatic bromoetherifications of straight-chain co-isolated unsaturated C15-diols – laurediols (3E,6R,7R)-7a and (3Z,6S,7S)-7b8 – to monocyclic medium-ring ethers deacetyl laurencin 1b and prelaureatin 2 respectively, albeit in very low yields (Scheme 1, top).[9]
We have recently advanced an alternative biogenesis for the monocyclic (C15H21BrO2) medium-ring ethers from Laurencia species from (6S,7R)-epoxide 8 via an intramolecular bromonium ion assisted epoxide ring-opening (IBIAERO) reaction with water functioning as the external nucleophile (Scheme 1, bottom, 8-B-O/O0-1b/2), and experimentally corroborated this with a model epoxide for the concurrent formation of 7, 8- and 9-ring ethers corresponding to the halogenated medium-ring ethers of known metabolites from Laurencia species.[10,11]
Summary
Proof-of-principle direct double cyclisation of a linear C15-precursor to a dibrominated bicyclic medium-ring ether relevant to Laurencia species†. Bicyclic dibrominated C15 medium-ring ether hexahydrolaureoxanyne was produced directly from an acyclic model C15-epoxide when treated with NBS with water as the solvent.
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