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Expedient construction of the Ziegler intermediate useful for the synthesis of forskolin via consecutive rearrangements.

Organic letters (2009-12-01)
Heping Ye, Gang Deng, Jun Liu, Fayang G Qiu
RESUMEN

The Ziegler intermediate, useful for the total synthesis of forskolin, was synthesized in 10 reaction steps starting from commercially available alpha-ionone. This highly efficient synthesis relies on the success of two consecutive highly regio- and stereoselective rearrangements. The current synthesis has not only established an efficient synthetic route to access the Ziegler intermediate but it has also paved a way to the structural optimization of forskolin.

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Sigma-Aldrich
α-Ionone, ≥90%, stabilized
Sigma-Aldrich
α-Ionone, technical grade, 90%