A New Route to Spirooxindoles

Abstract

[reaction: see text]Reaction of indole amides 5 with tributylstannane gave spiroindolenines 9 which are readily converted into spiropyrrolidinyloxindoles. This tricyclic system is found in a number of interesting natural products.

Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids

“…[43] Another interesting radical approach by Jones ultimately led to oxindoles with a higher degree of substitution at the pyrrolidine part. [44] Cossy used a very similar approach to access spiro[pyrrolidine-3,3Ј-oxindoles]. [45] Scheme 15.…”

Reaction of arylmethylidene derivatives of 3H-furan-2-ones with azomethine ylide

“…[1][2][3][4][5][6][7] In particular, spiro-and dispiropyrrolidines are important structural entities of many alkaloids and biologically active substances, 8,9 many of which are potential antiviral, anticancer, and anticonvulsant agents. 10,11 5-R-3-arylmethylidene-3H-furan-2-ones may be used as accessible and promising substrates in 1,3-dipolar cycloaddition reactions.…”

A First Resource‐Efficient and Highly Flexible Procedure for a Four‐Component Synthesis of Dispiropyrrolidines

“…99 (m, 1 H, H c ), 3.93-3.96 (m, 1 H, H b ), 3.52-3.56 (m, 1 H, H a ), 2.13 (s, 3 H, N-CH 3 ) ppm. 13 www.eurjoc.org 13 -4Ј-methyltrispiro[indane-2,3Ј-pyrrolidine-2Ј,3ЈЈ-indole]-1,3,2ЈЈ-trione (6o) , 8 H, ArH), 3.70-3.74 (m, 1 H, H c ), 3.36-3.40 (m, 1 H, H b ), 3.18-3.22 (m, 1 H, H a ), 2.04 (s, 3 H, N-CH 3 ), 0.75 (d, J = 7.5 Hz, 3 H, CH 3 ) ppm. 13 Hydroxybenzoyl)-1Ј-methyltrispiro[indane-2,3Ј-pyrrolidine-2Ј,2ЈЈ-acenaphthene]-1,3,1ЈЈ-trione (7i) Supporting Information (see footnote on the first page of this article): Detailed experimental procedures; copies of the spectra for all new compounds.…”

“…[12] Spiropyrrolidinyloxindoles are also found in a number of alkaloids of biological importance. [13] For example, spirotryprostatin A, a natural alkaloid isolated from the fermentation broth of Aspergillus fumigatus, has been identified as a novel inhibitor of microtubule assembly, and pteropodine and isopteropodine have been shown to modulate the function of muscarinic serotonin receptors ( Figure 1).…”