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(1'S,6'S,8'S,9'R)-9'-Bromo-12'-oxa-spiro-[1,3-dioxolane-2,4'-tricyclo-[6.3.1.0(1,6)]dodeca-ne].

ABSTRACT: In an endeavor directed towards the construction of the oxabicyclic[3.2.1]octane segment present in the bioactive natural products of cortistatins and icetexanes genre, the title compound, C(13)H(19)BrO(3), was synthesized from (4aR,9aS)-1,3,4,4a,5,6,9,9a-octa-hydro-spiro-[benzo[7]annulene-2,2'-[1,3]dioxolane]-4a-ol via a transannular bromo-etherification protocol. The six-membered ring adopts a twist-boat conformation, while the fused cycloheptane ring adopts a chair conformation. The crystal packing is effected through two distinct inter-molecular C-H?O hydrogen-bond patterns and mol-ecules are arranged to define an inter-esting motif along the b axis.

SUBMITTER: Mehta G

PROVIDER: S-EPMC3414332 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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(1'S,6'S,8'S,9'R)-9'-Bromo-12'-oxa-spiro-[1,3-dioxolane-2,4'-tricyclo-[6.3.1.0(1,6)]dodeca-ne].

Mehta Goverdhan G Khan Tabrez Babu TB

Acta crystallographica. Section E, Structure reports online 20120710 Pt 8

In an endeavor directed towards the construction of the oxabicyclic[3.2.1]octane segment present in the bioactive natural products of cortistatins and icetexanes genre, the title compound, C(13)H(19)BrO(3), was synthesized from (4aR,9aS)-1,3,4,4a,5,6,9,9a-octa-hydro-spiro-[benzo[7]annulene-2,2'-[1,3]dioxolane]-4a-ol via a transannular bromo-etherification protocol. The six-membered ring adopts a twist-boat conformation, while the fused cycloheptane ring adopts a chair conformation. The crystal p ...[more]

PMID: 22904865

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