Total Synthesis of (±)-Welwitindolinone A Isonitrile
- 11 January 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (5), 1448-1449
- https://doi.org/10.1021/ja057640s
Abstract
A highly stereoselective total synthesis of the alkaloid natural product welwitindolinone A isonitrile has been completed. The synthesis utilizes a chloronium ion mediated semi-pinacol rearrangement to simultaneously install the C10 quaternary center and neopentyl chlorine and a novel anionic cyclization to construct the spiro-oxindole with complete stereocontrol.Keywords
This publication has 7 references indexed in Scilit:
- A Mild and Efficient Synthesis of Oxindoles: Progress Towards the Synthesis of Welwitindolinone A IsonitrileAngewandte Chemie International Edition, 2004
- Welwitindolinones, Unusual Alkaloids from the Blue-Green Algae Hapalosiphon welwitschii and Westiella intricata. Relationship to Fischerindoles and HapalinodolesJournal of the American Chemical Society, 1994
- Improved protocols for the selective deprotection of trialkylsilyl ethers using fluorosilicic acidThe Journal of Organic Chemistry, 1993
- Synthesis and molecular structure of [7]circuleneJournal of the American Chemical Society, 1988
- Direct, regiospecific 2-lithiation of pyridines and pyridine 1-oxides with in situ electrophilic trappingThe Journal of Organic Chemistry, 1983
- α‐Metalated Isocyanides in Organic Synthesis. New synthetic methods (6)Angewandte Chemie International Edition in English, 1974
- Sulfuranes. III. Reagent for the dehydration of alcoholsJournal of the American Chemical Society, 1971