Alkynyliodonium Salts in Organic Synthesis. Application to the Preparation of the Tricyclic Core of (±)-Halichlorine
- 21 October 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (23) , 7928-7932
- https://doi.org/10.1021/jo0487911
Abstract
The tricyclic core of halichlorine has been synthesized through the use of an alkynyliodonium salt/alkylidenecarbene/1,5 C−H insertion sequence that sets the pivotal quaternary center in the target.Keywords
This publication has 41 references indexed in Scilit:
- Synthesis of 1-Azaspirocycles via Lewis Acid-Mediated Spirocyclization of Cyclic N-Acyl-N,O-acetalsSynlett, 2001
- Synthetic Studies on Halichlorine and Pinnaic Acid: Palladium-mediated Construction of the Bicyclic Spiro CoreHETEROCYCLES, 2001
- Synthetic Studies on Halichlorine and Pinnaic Acid. Stereospecific Preparation of the Azaspiro Core StructureOrganic Letters, 1999
- VCAM-1/α4-integrin adhesion pathway: Therapeutic target for allergic inflammatory disordersJournal of Allergy and Clinical Immunology, 1996
- A new method for the synthesis of cyclopentenones via the tandem Michael addition-carbene insertion reaction of .beta.-ketoethynyl(phenyl)iodonium saltsJournal of the American Chemical Society, 1994
- Preparation and chemistry of PhI+C.tplbond.CI+Ph.cntdot.2-OTf, bis[phenyl[[(trifluoromethyl)sulfonyl]oxy]iodo]acetylene, a novel difunctional acetylene, bis(iodonium) species and a stable C2-transfer agentJournal of the American Chemical Society, 1991
- Intramolecular hypervalent tin-oxygen interaction. The origin for fixation of six-membered carbocycles to the 1,3-diaxial conformer and for stereoselective osmylationsJournal of the American Chemical Society, 1988
- Desulfurization/.alpha.-alkylation of .beta.-keto sulfonesThe Journal of Organic Chemistry, 1985
- Alkyltin(IV)-mediated carbocyclizationJournal of the American Chemical Society, 1980
- Organoselenium chemistry. A facile one-step synthesis of alkyl aryl selenides from alcoholsThe Journal of Organic Chemistry, 1976