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Synthesis 2023; 55(12): 1940-1948
DOI: 10.1055/a-2012-5187
DOI: 10.1055/a-2012-5187
paper
Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry
Aza-Wacker Cyclization Toward the Bridged Core of FR901483
Financial support from the National Natural Science Foundation of China (22171281 and 22271194) and the Science and Technology Commission of Shanghai Municipality (20XD1404700) is greatly appreciated.
Abstract
A nine-step synthetic route to access the tricyclic core of FR901483 is reported, featuring a key aza-Wacker cyclization step to construct an α-tertiary amine (ATA) in the bridged structure. The aza-Wacker protocol can tolerate both exocyclic and endocyclic double bonds, providing viable access to various bridged bicyclic rings bearing an ATA (e.g., 6-azabicyclo[3.2.1]octane, 7-azabicyclo[3.3.1]nonane, and 7-azabicyclo[4.2.1]nonane) in good to excellent yields. The synthetic studies presented herein enable structural derivatization of FR901483 to further exploit its compelling biological activities.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2012-5187.
- Supporting Information
Publication History
Received: 24 December 2022
Accepted after revision: 13 January 2023
Accepted Manuscript online:
13 January 2023
Article published online:
06 February 2023
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For reviews on the synthesis of cephalotaxine, see:
For the total synthesis of FR901483, see:
For the formal synthesis of FR901483, see:
For the skeleton synthesis of FR901483, see:
For recent reviews on the bridged ring systems, see: