Authors: | Schmidt, Ann-Christin Hiersemann, Martin |
Title: | Total synthesis and structural assignment of (−)-fusaequisin A |
Language (ISO): | en |
Abstract: | (−)-Fusaequisin A is an irregularly assembled polyketide isolated from the ascomycete Fusarium equiseti. Fusaequisin A shares a carbon backbone with curvicollide C from the ascomycete Podospora curvicolla but its absolute configuration remained hitherto unsettled. Herein, we document the total synthesis of (−)-fusaequisin A and its 4-O-desmethyl derivative following a central-to-lateral building block strategy. Catalytic asymmetric Claisen rearrangement, Julia-Kocienski olefination and olefin cross-metathesis served as key C/C-connecting transformations. The constitution and absolute configuration of (−)-fusaequisin A was deduced and the original structural assignment was adjusted. |
Subject Headings: | Asymmetric synthesis Natural products Polyketides Structural elucidation Total synthesis |
URI: | http://hdl.handle.net/2003/40764 http://dx.doi.org/10.17877/DE290R-22621 |
Issue Date: | 2021-11-11 |
Rights link: | https://creativecommons.org/licenses/by-nc-nd/4.0/ |
Appears in Collections: | Organische Chemie |
Files in This Item:
File | Description | Size | Format | |
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Chemistry A European J - 2021 - Schmidt - Total Synthesis and Structural Assignment of ‐Fusaequisin A.pdf | DNB | 2.44 MB | Adobe PDF | View/Open |
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