Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial

doi:10.1016/j.cclet.2019.03.033

Chinese Chemical Letters

Volume 30, Issue 8, August 2019, Pages 1503-1505

https://doi.org/10.1016/j.cclet.2019.03.033 Get rights and content

Abstract

In this paper, we report the concise total syntheses of three botryane sesquiterpenoids: dehydrobotrydienal, dehydrobotrydienol, and 10-oxodehydrodihydrobotrydial. The key transformations include tandem Co-tetramethylthiourea-catalyzed Pauson–Khand and 6π-electrocyclization reactions to forge the tricyclic core structure of the botryanes, and further oxidative aromatization and oxidation to complete the total syntheses.

Graphical abstract

Concise total syntheses of dehydrobotrydienal, dehydrobotrydienol, and 10-oxodehydrodihydrobotrydial were accomplished via tandem Pauson–Khand and 6π-electrocyclization reactions.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Nos. 21772008, 21632002 and U1606403), Natural Science Foundation of Guangdong Province (No. 2016A030306011), Shenzhen Basic Research Program (Nos. JCYJ20170818090044432 and JCYJ20160226105337556) and Qingdao National Laboratory for Marine Science and Technology (No. LMDBKF201703).

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CommunicationTotal syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial

Abstract

Graphical abstract

Section snippets

Acknowledgments

Pure Appl. Chem.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Eur. J. Org. Chem.

J. Org. Chem.

Org. Lett.

Angew. Chem. Int. Ed.

Phytochemistry

Nat. Prod. Rep.

Curr. Org. Chem.

Chem. Ber.

Photochemistry

Photochemistry

Photochemistry

Photochemistry

J. Nat. Prod.

Communication
Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial