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Synthesis 2021; 53(16): 2874-2880
DOI: 10.1055/a-1478-9088
paper

First Total Synthesis of 27-Deoxylyngbyabellin A

Yang Zhang
a   State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Yi Liu  ∗
b   School of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, P. R. of China
,
Yuguo Du∗
a   State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China
c   School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
› Author AffiliationsThis 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).
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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 agents

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1478-9088.
  • Supporting Information

Primary Data



Publication History

Received: 21 March 2021

Accepted after revision: 09 April 2021

Accepted Manuscript online:
09 April 2021

Article published online:
03 May 2021

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