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Synlett 2024; 35(04): 423-426
DOI: 10.1055/a-2102-8014
DOI: 10.1055/a-2102-8014
cluster
11th Singapore International Chemistry Conference (SICC-11)
Toward the Total Synthesis of Schinortriterpenoids: Construction of the All-cis-Substituted Cyclopropane Unit
This work was financially supported by a grant from JSPS KAKENHI (Grant Number JP21H02131) to C.T. This work was also supported by JST, the establishment of university fellowships towards the creation of science technology innovation, Grant Number JPMJFS2123.
Abstract
As a step toward a total synthesis of pre-schisanartanins and arisanlactones, we successfully synthesized a right fragment of Schisandra nortriterpenoids bearing a distorting all-cis-substituted cyclopropane from a chiral lactone. The key step in this synthesis was the diastereoselective construction of an all-cis-substituted cyclopropane through a Negishi coupling using an amide as a directing group.
Key words
cyclopropanes - nortriterpenoids - Negishi coupling - pre-schisanartanins - arisanlactones - diastereoselective synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2102-8014.
- Supporting Information
Publication History
Received: 09 May 2023
Accepted after revision: 30 May 2023
Accepted Manuscript online:
30 May 2023
Article published online:
10 July 2023
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