Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system

Graham J Bodwell; Jiang Li

doi:10.1021/ol017014+

Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system

Org Lett. 2002 Jan 10;4(1):127-30. doi: 10.1021/ol017014+.

Authors

Graham J Bodwell¹, Jiang Li

Affiliation

¹ Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada, A1B 3X7. gbodwell@mun.ca

PMID: 11772107
DOI: 10.1021/ol017014+

Abstract

[reaction: see text] The title compound was synthesized concisely from indole. A 2-fold sequential hydroboration/Suzuki-Miyaura cross-coupling was employed to generate the cyclophane. When heated in N,N-diethylaniline, it underwent a transannular inverse electron demand Diels-Alder (IEDDA) reaction to form a pentacyclic product, which appears to be well suited as a precursor to a variety of indole alkaloids such as strychnine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Indicators and Reagents
Indoles / chemical synthesis*
Polycyclic Compounds / chemical synthesis
Pyridazines / chemical synthesis*
Pyridazines / chemistry

Substances

(3)(3,6)pyridazino(3)(1,3)indolophane
Indicators and Reagents
Indoles
Polycyclic Compounds
Pyridazines