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Synthesis 2016; 48(11): 1727-1733
DOI: 10.1055/s-0035-1561581
DOI: 10.1055/s-0035-1561581
paper
Synthesis of Isochroman Derivatives via Oxa-Pictet–Spengler Reaction of Vinylogous Esters
Authors
Weitere Informationen
Publikationsverlauf
Received: 30. November 2015
Accepted after revision: 16. Februar 2016
Publikationsdatum:
17. März 2016 (online)
Abstract
Trimethylsilyl triflate (TMSOTf) can be efficiently used for the synthesis of isochromans via Pictet–Spengler type reaction of vinylogous esters in good yields. The methodology is applied for the formal synthesis of key intermediate alcohols for the synthesis of D4 antagonist sonepiprazole (±)-U-101387 and the isochroman (±)-U-54537.
Key words
isochroman - oxa-Pictet–Spengler reaction - vinylogous esters - cyclization - D4 antagonistSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561581.
- Supporting Information (PDF)
-
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