Total Synthesis of (−)-Herbindoles A, B, and C via Transition-Metal-Catalyzed Intramolecular [2 + 2 + 2] Cyclization between Ynamide and Diynes
- 27 March 2012
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (7) , 1914-1917
Abstract
The total syntheses of (−)-herbindoles A, B, and C as naturally occurring forms were accomplished for the first time through transition-metal-catalyzed intramolecular [2 + 2 + 2] cyclization between ynamide and diynes. This strategy provided a highly efficient synthetic route to all three herbindoles from an identical indoline derivative as a common intermediate.Keywords
This publication has 68 references indexed in Scilit:
- Gold‐Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with AlkenesAngewandte Chemie International Edition, 2011
- Introducing a New Class of N-Phosphoryl Ynamides via Cu(I)-Catalyzed Amidations of Alkynyl BromidesOrganic Letters, 2011
- Intermolecular and Selective Synthesis of 2,4,5‐Trisubstituted Oxazoles by a Gold‐Catalyzed Formal [3+2] CycloadditionAngewandte Chemie International Edition, 2011
- N-Allyl-N-sulfonyl Ynamides as Synthetic Precursors to Amidines and Vinylogous Amidines. An Unexpected N-to-C 1,3-Sulfonyl Shift in Nitrile SynthesisThe Journal of Organic Chemistry, 2011
- Synthesis of 2-iodoynamides and regioselective [2+2] cycloadditions with keteneTetrahedron Letters, 2011
- Synthesis of Polycyclic Benzofused Nitrogen Heterocycles via a Tandem Ynamide Benzannulation/Ring-Closing Metathesis Strategy. Application in a Formal Total Synthesis of (+)-FR900482The Journal of Organic Chemistry, 2011
- Ynamides: A Modern Functional Group for the New MillenniumChemical Reviews, 2010
- Concise Total Synthesis of (±)-cis-Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne CycloadditionOrganic Letters, 2008
- Highly Stereo- and Regioselective Synthesis of (Z)-Trisubstituted Alkenes via 1-Bromo-1-alkyne Hydroboration−Migratory Insertion−Zn-Promoted Iodinolysis and Pd-Catalyzed Organozinc Cross-CouplingJournal of the American Chemical Society, 2007
- Preparation of Alkyl-Substituted Indoles in the Benzene Portion. Part 11. Total Synthesis of (6R,8S)-Herbindole A, (6R,8S)-Herbindole B, (6R,8S)-Herbindole C, (6R,8S)-cis-Trikentrin A, (6R,8S)-cis-Trikentrin B, (6R,8R)-trans-Trikentrin B, and (6R,8R)-iso-trans-Trikentrin B. Determination of the Absolute Structures of Natural Herbindoles and Trikentrins.Chemical and Pharmaceutical Bulletin, 1994