A synthetic approach to enfumafungin |
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Authors: | Nicolas Zorn |
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Affiliation: | Unité Mixte CNRS-AVENTIS Pharma (UMR 26) 102, route de Noisy, 93235 Romainville, France |
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Abstract: | The stereospecific synthesis of the dienophile subunits 5 was achieved from the butenolide 6. Ester 19 was obtained in 67% overall yield (2 steps), with no intermediate purification, by a sodium chlorite oxidation of the corresponding aldehyde in buffered conditions, followed immediately after extraction, by a Mitsunobu reaction of the relatively labile acid 3 with alcohol 13. The synthesis of the α,β-unsaturated aldehydes 22 and 23 is also reported. Tentative IMDA reactions of 22 and 23 were examined in thermal conditions, or with a Lewis acid catalysis, and results are reported herein. |
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