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DOI: 10.1055/a-1478-9088
First Total Synthesis of 27-Deoxylyngbyabellin A
This work was supported in part by the National Key Research and Development Program of China (2019YFC1605802), the Natural Science Foundation of Shandong Province (ZR2020MB105), and the National Natural Science Foundation of China (NNSFC, 21402192).
Abstract
In this study, we document the first total synthesis of the marine cyanobacteria secondary metabolite 27-deoxylyngbyabellin A in 10 linear steps with 9.7% overall yield. Key steps entailed (1) one-pot cascade reaction of (S)-2-(benzyloxy)-3-methylbutanoic acid and of Boc-l-Ile-OH with a β-azido disulfide building block to access two critical thiazole units, (2) chiral oxazaborolidinone-mediated asymmetric aldol reaction to construct an (S)-β-hydroxy ester, and (3) diphenyl phosphorazidate mediated macrolactamization of the assembled linear precursor to achieve the natural product 27-deoxylyngbyabellin A.
Key words
total synthesis - cyclic peptides - 27-deoxylyngbyabellin A - thiazoles - antitumor agentsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1478-9088.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at https://zenodo.org/record/4680006 and can be cited using the following DOI: 10.5281/zenodo.4680006.
Publikationsverlauf
Eingereicht: 21. März 2021
Angenommen nach Revision: 09. April 2021
Accepted Manuscript online:
09. April 2021
Artikel online veröffentlicht:
03. Mai 2021
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