Enantioselective Synthesis of Octahydrofuranoindole Core of Aspidosperma Alkaloids via Diels Alder/Reduction-/Fluoroetherification Reactions Sequence

Herein, we disclose the enantioselective synthesis of novel tricyclic fluorooctahydrofuranoindole spirooxindoles bearing five contiguous stereocenters via organocatalytic sequential Diels-Alder/Reduction/Fluoroetherifiction reaction strategy. The potential of the developed approach was witnessed by...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2023-07, p.e202300419
Main Authors: Madavi, Shiva Prasad, Sankar, Bharani, JhA, Aman Kumar, Sugali, Chetan Nayak, Murugesan, Sivaprakash, L, Raju Chowhan
Format: Article
Language:English
Online Access:Get full text
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Summary:Herein, we disclose the enantioselective synthesis of novel tricyclic fluorooctahydrofuranoindole spirooxindoles bearing five contiguous stereocenters via 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 71% 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).
ISSN:1861-471X
DOI:10.1002/asia.202300419