Total Synthesis and Revision of Stereochemistry of a Natural Benzo[ g ]isochromene Stereodiad Isolated from Rubia philippinensis .

Autor: Choudhury R; Organic Chemistry Division, Council of Scientific and Industrial Research (CSIR)-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Miriyala SRT; Department of Organic Synthesis & Process Chemistry, Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Resmi KR; Centre for X-ray Crystallography, Department of Analytical & Structural Chemistry, Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India., Sridhar B; Centre for X-ray Crystallography, Department of Analytical & Structural Chemistry, Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Kasa SRKM; Daicel Chiral Technologies (India) Private Limited, Hyderabad 500101, India., Reddy DS; Department of Organic Synthesis & Process Chemistry, Council of Scientific and Industrial Research (CSIR)-Indian Institute of Chemical Technology (IICT), Hyderabad 500007, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Apr 05; Vol. 26 (13), pp. 2574-2579. Date of Electronic Publication: 2024 Mar 21.
DOI: 10.1021/acs.orglett.4c00553
Abstrakt: This study presents a total synthesis and revision of the stereochemical configuration of the conformationally flexible natural product benzo[ g ]isochromene stereodiad alongside its diastereomeric counterparts. The highlights of the synthesis are the TiCl 4 -mediated diastereoselective aldol reaction, Pd-catalyzed lactonization, and Schmidt glycosidation. Our efforts using total synthesis disclosed herein proved that a previously assigned structure required revision.
Databáze: MEDLINE
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