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Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

ABSTRACT: A total synthesis of the unusual ent-kaurane maoecrystal V is described. The synthesis strategy features a counterintuitive early disconnection of the lactone subunit to a polycyclic enol ether intermediate in order to preserve the central tetrahydrofuran ring until the beginning stages of the synthesis. This strategy enables an application of C-H functionalization at the early phase of the synthesis during the construction of a dihydrobenzofuran intermediate.

SUBMITTER: Lu P

PROVIDER: S-EPMC4118676 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Total synthesis of maoecrystal V: early-stage C-H functionalization and lactone assembly by radical cyclization.

Lu Ping P Gu Zhenhua Z Zakarian Armen A

Journal of the American Chemical Society 20130923 39

A total synthesis of the unusual ent-kaurane maoecrystal V is described. The synthesis strategy features a counterintuitive early disconnection of the lactone subunit to a polycyclic enol ether intermediate in order to preserve the central tetrahydrofuran ring until the beginning stages of the synthesis. This strategy enables an application of C-H functionalization at the early phase of the synthesis during the construction of a dihydrobenzofuran intermediate. ...[more]

PMID: 24047444

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