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Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes.

ABSTRACT: Daphnanes and tiglianes are diterpenes with a shared tricyclic 5-7-6 ring system. Many members exhibit significant biological activities often associated with protein kinase C signaling. Many of these natural products (~100) have a C6-C7 ?-epoxide whose influence on biological activity is little studied. Using the more readily available phorbol ester PDBu as a test substrate, we report an efficient, and potentially general, ?-epoxidation method based on a vanadium-catalyzed asymmetric epoxidation with bishydroxamic acid (BHA) ligands.

SUBMITTER: Boudreault PL

PROVIDER: S-EPMC4449265 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes.

Boudreault Pierre-Luc PL Mattler Jennifer K JK Wender Paul A PA

Tetrahedron letters 20150601 23

Daphnanes and tiglianes are diterpenes with a shared tricyclic 5-7-6 ring system. Many members exhibit significant biological activities often associated with protein kinase C signaling. Many of these natural products (~100) have a C6-C7 α-epoxide whose influence on biological activity is little studied. Using the more readily available phorbol ester PDBu as a test substrate, we report an efficient, and potentially general, α-epoxidation method based on a vanadium-catalyzed asymmetric epoxidatio ...[more]

PMID: 26034334

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