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Enantioselective Total Synthesis of the Diterpene (+)-Cubitene^†

Dr. Kristina Simon

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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M. Sc. Johannes Wefer,

M. Sc. Johannes Wefer

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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Dr. Elisabeth Schöttner,

Dr. Elisabeth Schöttner

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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Prof. Dr. Thomas Lindel,

Corresponding Author

Prof. Dr. Thomas Lindel

[email protected]

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel Search for more papers by this author

Dr. Kristina Simon,

Dr. Kristina Simon

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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M. Sc. Johannes Wefer,

M. Sc. Johannes Wefer

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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Dr. Elisabeth Schöttner,

Dr. Elisabeth Schöttner

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

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Prof. Dr. Thomas Lindel,

Corresponding Author

Prof. Dr. Thomas Lindel

[email protected]

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig (Germany) http://www.oc.tu-bs.de/lindel Search for more papers by this author

First published: 25 September 2012

https://doi.org/10.1002/anie.201205143

Citations: 15

^†

Financial support by the Deutsche Forschungsgemeinschaft (DFG, Li 597/4–1) and the Fonds der Chemischen Industrie (FCI, stipend to J.W.) is gratefully acknowledged. We also thank Merck KGaA (Germany) for chromatography materials. BASF AG and Honeywell Specialty Chemicals Seelze GmbH are thanked for the donation of solvents.

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Graphical Abstract

From termite soldier's secretions: The enantioselective total synthesis of the diterpene (+)-cubitene is described. The route is characterized by the cyclization of a carvone-derived C₂₀ allylphosphate with SmI₂, followed by fragmentation to the twelve-membered ring. As a result, perfect stereocontrol of the isopropenyl-substituted positions is achieved.

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Volume51, Issue43

October 22, 2012

Pages 10889-10892

Enantioselective Total Synthesis of the Diterpene (+)-Cubitene^†

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Enantioselective Total Synthesis of the Diterpene (+)-Cubitene†

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Enantioselective Total Synthesis of the Diterpene (+)-Cubitene^†