Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system

Authors
Wang, JJ Rosingana, M Watson, DJ Dowdy, ED Discordia, RP Soundarajan, N Li, WS
Citation
Jj. Wang et al., Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system, TETRAHEDR L, 42(51), 2001, pp. 8935-8937
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
8935 - 8937
Database
ISI
SICI code
0040-4039(200112)42:51<8935:PSOTRA>2.0.ZU;2-4
Abstract
Using atmospheric O-2 as the stoichiometric oxidant, Pd2+/Cu2+-catalyzed ox idative cyclization of the corresponding bisindolylmaleimides provides the rebeccamycin aglycone and related indolo[2,3-a]pyrrolo[3,4-c]carbazoles in 58-88% yield. The method is operationally simple and utilizes readily prepa red substrates, making the process amenable to scaleup. (C) 2001 Elsevier S cience Ltd. All rights reserved.