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Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids

Zhao, J; Méndez-Sánchez, D; Ward, JM; Hailes, HC; (2019) Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids. The Journal of Organic Chemistry , 84 (12) pp. 7702-7710. 10.1021/acs.joc.9b00527. Green open access

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Abstract

Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet-Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1'-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this approach. This study features the role of phosphate in the aqueous-based PSR and provides an atom-efficient, sustainable route to new THIQs.

Type: Article
Title: Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.joc.9b00527
Publisher version: https://doi.org/10.1021/acs.joc.9b00527
Language: English
Additional information: © 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html).
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10075595
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