Synthesis of nor-sesquiterpene spirolactones and their steroidal hybrids revisited. The neopentyl dilemma: misassignment of one stereocentre may necessitate a completely new approach
| Autor: | Ramkrishna Basak, Angeline Chanu, Siméon Arseniyadis, Zobida Elkhayat, Imad Safir |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Ketone [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Organic Chemistry 010402 general chemistry Sesquiterpene 01 natural sciences Combinatorial chemistry Microwave assisted Catalysis 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Mitsunobu reaction Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Tetrahedron: Asymmetry Tetrahedron: Asymmetry, Elsevier, 2014, 25 (18-19), pp.1253-1263. ⟨10.1016/j.tetasy.2014.08.005⟩ |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2014.08.005 |
| Popis: | Inversion at the highly congested C1 position of 1-epi-pathylactone A (1-epi-1), or its corresponding steroidal hybrid 8a, using a diverse range of published procedures including microwave assisted Mitsunobu reaction or via oxidation to the corresponding ketone and subsequent reduction, was unsuccessful in our hands. Attempts to convert the C1 hydroxyl group into its corresponding chloride, en route to napalilactone 2a, also failed. Precursors with the C1α configuration installed at early stage proved not to be amenable to the targets under a broad range of conditions. |
| Databáze: | OpenAIRE |
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