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Synfacts 2025; 21(11): 1081
DOI: 10.1055/a-2703-1054
DOI: 10.1055/a-2703-1054
Synthesis of Natural Products
Total Synthesis of (–)-FR182877
Authors
Evans DA *,
Starr JT.
Harvard University, Cambridge, USA
A Cycloaddition Cascade Approach to the Total Synthesis of (−)-FR182877.
J. Am. Chem. Soc. 2003;
125: 13531-13540
DOI: 10.1021/ja037643+
A Cycloaddition Cascade Approach to the Total Synthesis of (−)-FR182877.
J. Am. Chem. Soc. 2003;
125: 13531-13540
DOI: 10.1021/ja037643+
Keywords
(–)-FR182877 - polyketide synthesis - Suzuki–Miyaura coupling - Roskamp homologation - Appel reaction - macrocylization - transannular Diels–Alder reaction - inverse-electron-demand hetero-Diels–Alder reaction - Suzuki methylenation - Mukaiyama lactonization
Significance
Evans and Starr reported the total synthesis of (–)-FR182877, a polyketide exhibiting potent antitumor activity. After close analysis of the isolation data, the authors reassigned the absolute configuration of the compound in a previous report.
Comment
The strategy to build the hexacyclic core of the natural product relied on a cyclization cascade including a transannular Diels–Alder reaction of macrocycle G followed by inverse-electron-demand hetero-Diels–Alder reaction.
Publication History
Article published online:
30 October 2025
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