Enantioselective Synthesis of Octahydrofuranoindole Core of Aspidosperma Alkaloids via a Diels-Alder/Reduction/Fluoroetherification Reaction Sequence.

Autor: Prasad MS; Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN)., Tiruvarur, 610 005, India., Bharani MS; Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN)., Tiruvarur, 610 005, India., Jha MAK; Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN)., Tiruvarur, 610 005, India., Naik MSC; Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN)., Tiruvarur, 610 005, India., Sivaprakash M; Asymmetric synthesis and catalysis laboratory, Department of Chemistry, Central University of Tamil Nadu (CUTN)., Tiruvarur, 610 005, India., Chowhan LR; School of Physical Sciences, Jawaharlal Nehru University, New Delhi, 110067, India.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2023 Aug 15; Vol. 18 (16), pp. e202300419. Date of Electronic Publication: 2023 Jul 20.
DOI: 10.1002/asia.202300419
Abstrakt: Herein, we disclose the enantioselective synthesis of novel tricyclic fluorooctahydrofuranoindole spirooxindoles bearing five contiguous stereocenters via an organocatalytic sequential Diels-Alder/Reduction/Fluoroetherifiction reaction strategy. The potential of the developed approach was witnessed by generating vast examples (up to 20 examples) of library molecules embedding natural product core with good yields and phenomenal diastereo- and enantioselectivities (up to 77 % overall yield, up to 99 % ee and 10 : 1 dr). The synthetic utility of our protocol was further demonstrated by synthesizing tricyclic iodooctahydroindole spirooxindole framework through sequential Diels-Alder/reduction/iodoetherification reaction in 65 % overall yield and excellent stereoselectivity (99 % ee and 4 : 1 dr).
(© 2023 Wiley-VCH Verlag GmbH.)
Databáze: MEDLINE
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