A photocycloaddition/fragmentation approach toward the 3,12- dioxatricyclo[8.2.1.06,13]tridecane skeleton of terpenoid natural products

Jörg P. Hehn; Eberhardt Herdtweck; Thorsten Bach

doi:10.1021/ol2004462

A photocycloaddition/fragmentation approach toward the 3,12- dioxatricyclo[8.2.1.0^6,13]tridecane skeleton of terpenoid natural products

Jörg P. Hehn
, Eberhardt Herdtweck
, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

Starting from tetronate 1 (R = CH₂OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.0^6,13]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).

Original language	English
Pages (from-to)	1892-1895
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	7
DOIs	https://doi.org/10.1021/ol2004462
State	Published - 1 Apr 2011

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abstract = "Starting from tetronate 1 (R = CH2OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.06,13]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).",

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AU - Herdtweck, Eberhardt

AU - Bach, Thorsten

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AB - Starting from tetronate 1 (R = CH2OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.06,13]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).

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A photocycloaddition/fragmentation approach toward the 3,12- dioxatricyclo[8.2.1.0^6,13]tridecane skeleton of terpenoid natural products

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