One-Step Convergent Synthesis of the Steroid Ring System via the Coupling of γ,δ-Unsaturated Fischer Carbene Complexes with o-Ethynylbenzaldehyde
- 4 October 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (22) , 3535-3538
- https://doi.org/10.1021/ol0166404
Abstract
Simultaneous and stereoselective construction of the steroid B and C rings is observed in a tandem process involving the coupling of o-ethynylbenzaldehyde with 2-alkenylcyclopentylcarbene−chromium complexes.Keywords
This publication has 11 references indexed in Scilit:
- Unusual polyoxygenated sterols from a Philippines sponge Xestospongia sp.Tetrahedron, 2001
- New Cyclic Derivatives of 3?-Amino-3?-deoxy-adenosine-5?-diphosphate, -triphosphate, and -methylenebis(phosphonate)Angewandte Chemie International Edition in English, 1994
- Steroid total synthesisNatural Product Reports, 1994
- Free radical ring expansion of fused cyclobutanones: a new ring expansion annulation stratagemJournal of the American Chemical Society, 1991
- Improved synthesis of (aminocarbene)chromium(0) complexes with use of C8K-generated Cr(CO)52-. Multivariant optimization of an organometallic reactionOrganometallics, 1990
- Synthesis and electrochemistry of pyrimidoquinazoline-5,10-diones. Design of hydrolytically stable high potential quinones and new reductive alkylation systemsThe Journal of Organic Chemistry, 1988
- Preparation of acylpentacarbonylchromate salts and alkoxycarbene pentacarbonyl complexes of chromium employing the pentacarbonylchromate dianion ([Cr(CO)5]2-)Organometallics, 1987
- Steroid total synthesisRecueil des Travaux Chimiques des Pays-Bas, 1986
- Conformational analysis and stability of substituted 4-hydrindanones. A thermodynamic and magnetic resonance (proton and carbon-13) studyThe Journal of Organic Chemistry, 1981
- A remarkably simple, highly efficient, and stereoselective synthesis of steroids and other polycyclic systems. Total synthesis of estra-1,3,5(10)-trien-17-one via intramolecular capture of o-quinodimethanes generated by cheletropic elimination of sulfur dioxideThe Journal of Organic Chemistry, 1980