Issue 17, 2018

Synthesis of cassane-type diterpenes from abietane compounds: the first synthesis of taepeenin F

Abstract

The first synthesis of the aromatic cassane-type diterpene taepeenin F from abietic acid is reported. The key steps of the synthetic sequence are the ipso-substitution of the isopropyl group of a dehydroabietane derivative by a formyl group, after treatment with Cl2CHOMe and AlCl3, and the oxidative cleavage of a dihydronaphthalene intermediate. The deisopropylation reaction of dehydroabietane derivatives is revised and a complementary study on this subject is included. A mechanism for this reaction is postulated.

Graphical abstract: Synthesis of cassane-type diterpenes from abietane compounds: the first synthesis of taepeenin F

Supplementary files

Article information

Article type
Research Article
Submitted
20 Jun 2018
Accepted
24 Jul 2018
First published
25 Jul 2018

Org. Chem. Front., 2018,5, 2537-2541

Synthesis of cassane-type diterpenes from abietane compounds: the first synthesis of taepeenin F

P. Gutierrez, J. Altarejos, P. J. Linares-Palomino, R. Chahboun and E. Alvarez-Manzaneda, Org. Chem. Front., 2018, 5, 2537 DOI: 10.1039/C8QO00603B

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