Synthesis 2016; 48(11): 1727-1733
DOI: 10.1055/s-0035-1561581
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isochroman Derivatives via Oxa-Pictet–Spengler Reaction of Vinylogous Esters

Sujit Sarkar
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India   Email: asaikia@iitg.ernet.in
,
Sabera Sultana
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India   Email: asaikia@iitg.ernet.in
,
Kiran Indukuri
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India   Email: asaikia@iitg.ernet.in
,
Ramanjaneyulu Unnava
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India   Email: asaikia@iitg.ernet.in
,
Anil K. Saikia*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India   Email: asaikia@iitg.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 30 November 2015

Accepted after revision: 16 February 2016

Publication Date:
17 March 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.

Supporting Information

 
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