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Synthesis 2019; 51(03): 780-786
DOI: 10.1055/s-0037-1610997
DOI: 10.1055/s-0037-1610997
paper
Total Synthesis of 5-Hydroxygoniothalamin
Further Information
Publication History
Received: 13 July 2018
Accepted after revision: 05 September 2018
Publication Date:
01 October 2018 (online)
Abstract
The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l-xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis-Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.
Key words
C1 Wittig reaction - C2 Wittig reaction - Yamaguchi reaction - cross-metathesis - 5-hydroxygoniothalaminSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610997.
- Supporting Information
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