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An enantioselective total synthesis of aspergillides A and B has been accomplished on the basis of a unified synthetic strategy that exploits stereodivergent intramolecular oxa-conjugate cyclization and Yamaguchi macrolactonization. 相似文献
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Jhillu Singh Yadav Anand Kumar MishraSoma Shekar Dachavaram S. Ganesh KumarSaibal Das 《Tetrahedron letters》2014
A convergent enantioselective synthesis of penicimarin B, aspergillumarin A and B has been reported using Brown’s allylation, DeBrabander–Bhattacharjee lactonization and Grubbs cross coupling metathesis. During this synthesis we have standardized the conditions for DeBrabande–Bhattacharjee lactonization to obtain excellent yield (>90%). 相似文献
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The first enantioselective total synthesis of(+)-preussin B and an improved synthesis of the antifungal alkaloid(+)-preussin are described. Our approach relied on the four step-economical synthetic methods developed in our laboratory:(1) the cis-diastereoselective reductive dehydroxylation of hemiaminals;(2) the direct amide/lactam reductive alkylation;(3) the one-pot N,O-bisdebenzylation-N-methylation; and(4) the one-step synthesis of malimide from malic acid. Both total syntheses are quite concise, which have been achieved in six steps, and gave overall yields of 25.7% and 27.6%, respectively. 相似文献
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The title compound was synthesized through an expeditious route using Crimmins aldolization to establish the two key stereogenic centers and a hydroxyl group activation (HGA) protocol to construct the anti alpha,beta-disubstituted beta-lactone from the corresponding syn aldol. 相似文献
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[formula: see text] A concise asymmetric synthesis of the indole alkaloid (+)-geissoschizine (1) has been completed. The synthesis features the highly diastereoselective vinylogous Mannich reaction of 3 with 4 to give 5, which is elaborated into the key tetracyclic intermediate 7 in two steps. Following the stereoselective introduction of the ethylidene moiety to give 9, reduction of the lactam and radical decarboxylation via an acyl selenide gave 12, which was converted into (+)-geissoschizine by formylation. The synthesis requires only 11 chemical operations and proceeds in an overall yield of 17%. 相似文献
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A new efficient enantioselective synthetic method of (+)-isonitramine is reported. (+)-Isonitramine was obtained in 12 steps (98% ee and 43% overall yield) from δ-valerolactam via enantioselective phase-transfer catalytic alkylation, Dieckman condensation, and diastereoselective reduction as key steps. 相似文献
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[reaction: see text] The enantioselective total synthesis of (+)-allocyathin B(2) has been achieved. Our approach features a convergent enantioselective construction of the 5-6-7 tricyclic core system using the originally developed chiral building blocks via asymmetric catalysis, the intramolecular aldol reaction in high yield, successful samarium diiodide-mediated ring expansion, and a newly developed double-bond installation method. 相似文献
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Hao Wu 《Tetrahedron》2007,63(28):6454-6461
An enantioselective and convergent total synthesis of marine natural product pinnaic acid has been achieved. Our general synthetic approach is featured with an asymmetric hydrogenation of racemic γ-keto ester 3, a diastereoselective methylation on the α-methylene of the (1R,5R)-lactone 4, and a diastereoselective Michael addition of the tertiary nitro cyclopentane. The central azaspiro[4.5]decane was constructed utilizing reductive cyclization of the δ-nitroketone followed by highly stereoselective reduction of the cyclic imine with NaBH4. Ultimately, successive use of triethyl-2-phosphonopropionate and Heathcock's phosphorane 18 to elaborate C5 and C13 side chains completed the total synthesis of pinnaic acid. 相似文献
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A concise and enantioselective total synthesis of (+)-aigialospirol is described here, featuring the first complex natural product synthesis that employs a cyclic ketal-tethered ring-closing metathesis strategy and an unexpected stereoselective epimerization of a benzylic hydroxyl group. The 15-step synthetic sequence illustrates the proof-of-concept that such an approach can be competitive with the classical spiroketal formation in the natural product synthesis. 相似文献
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A catalytic enantioselective total synthesis of adociacetylene B (2) in five steps is reported. The efficiency of this synthesis was enabled by an asymmetric zinc alkynylation catalyzed by the proline-derived ligand (1). 相似文献
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[reaction: see text] A practical total synthesis of Bengamides B, E, and Z from a common polyol intermediate is described. Consecutive aldol condensations afford a protected polyol thioester side chain suitable for coupling to the Bengamides. A novel chiral phase transfer catalyzed enantioselective alkylation affords the more highly functionalized amino caprolactams required for Bengamides B and Z. Use of the 2-naphthylmethyl ether protecting group, compatible with the boron Lewis acids required for enantioselective aldol condensation, allows direct access to Bengamide B. 相似文献
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The enantioselective synthesis of the eunicellin ophirin B has been completed. A ring-closing metathesis provides efficient access to the oxonene ring, and a highly diastereoselective intramolecular Diels-Alder reaction results in the formation of the hydrobenzofuran portion of the molecule. 相似文献
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A new regio- and stereocontrolled total synthesis of the antibiotic strobilurin B is performed in nine steps in 5.5% overall yield. 相似文献
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Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation in high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrubiellone C, which led to the assignment of the configuration of the natural product as (R). 相似文献
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A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric centre, facilitating the rapid and diastereoselective construction of this functionalised system. 相似文献
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[reaction: see text] Pantocin B, an unusual antibiotic produced by Erwinia herbicola, effectively controls E. amylovora, the pathogen causing the plant disease fire blight. A total synthesis of pantocin B from L-alanine, glycine, and L-malic acid is reported. 相似文献
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[reaction: see text] Starting from 4,4-dimethyl-2-cyclohexenone, an efficient total synthesis of ricciocarpin A (1) in natural form has been accomplished. 相似文献