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Issue 7, 2020
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Synthesis of tricyclo[7.2.1.09,10]dodecan-11-one core ring systems of norditerpenoid alkaloids and racemulosine

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Abstract

A robust and convergent synthetic approach for the rapid assembly of common bridged tricyclic BCD-ring systems of norditerpenoid alkaloids as well as racemulosine has been developed. The synthesis features an efficient Au(I)-catalyzed [2 + 2] enyne cycloaddition and an exquisite pinacol rearrangement in a highly exclusive manner to generate the unique bicyclo[3.2.1]octane moiety of the CD-ring on the seven-membered B-ring.

Graphical abstract: Synthesis of tricyclo[7.2.1.09,10]dodecan-11-one core ring systems of norditerpenoid alkaloids and racemulosine

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Article information


Submitted
17 Jan 2020
Accepted
25 Feb 2020
First published
27 Feb 2020

Org. Chem. Front., 2020,7, 933-937
Article type
Research Article

Synthesis of tricyclo[7.2.1.09,10]dodecan-11-one core ring systems of norditerpenoid alkaloids and racemulosine

S. Cao, H. Yue, M. Zhu and L. Xu, Org. Chem. Front., 2020, 7, 933
DOI: 10.1039/D0QO00088D

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