2018
DOI: 10.1002/ejoc.201800026
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Divergent Synthesis of Bioactive Marine Meroterpenoids by Palladium‐Catalyzed Tandem Carbene Migratory Insertion

Abstract: The divergent synthesis of (+)‐8‐epi‐puupehedione, (+)‐chromazonarol, (+)‐yahazunol, and (+)‐yahazunone has been accomplished. The key steps were a palladium‐catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazone, a highly regioselective enol reduction, an oxa‐Stork–Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes.

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Cited by 28 publications
(22 citation statements)
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“…The total synthesis of yahazunol (137) and chromazonarol (43) was achieved starting from p-toluenesulfonyl hydrazide. The key steps were a palladiumcatalyzed tandem carbene migratory insertion of an aryl iodide and a drimanalhydrazone, a highly regionselective enol reduction, an oxa-Stork-Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes [105]. While the total synthesis of yahazunol (137), isozonarone (142), and zonarone (138) were starting from (+)-albicanic acid.…”
Section: Dictyopteris Undulata Holmes 1896mentioning
confidence: 99%
“…The total synthesis of yahazunol (137) and chromazonarol (43) was achieved starting from p-toluenesulfonyl hydrazide. The key steps were a palladiumcatalyzed tandem carbene migratory insertion of an aryl iodide and a drimanalhydrazone, a highly regionselective enol reduction, an oxa-Stork-Danheiser transposition reaction, an electrocyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes [105]. While the total synthesis of yahazunol (137), isozonarone (142), and zonarone (138) were starting from (+)-albicanic acid.…”
Section: Dictyopteris Undulata Holmes 1896mentioning
confidence: 99%
“…The palladium-catalyzed tandem carbene migratory insertion of an aryl iodide and a drimanal hydrazine of the intermediate 2 was also developed. 13 The trifluoromethane sulfonate 4 synthesized from R-carvone was successfully used to construct the central framework via Stille carbonylative cross-coupling reaction and Michael cyclization. 14 Sclareol oxide was converted to the diene 5 in the Diels-Alder cycloaddition approach.…”
Section: Scheme 1 Previous Approaches To Drimane (Hydro)quinonesmentioning
confidence: 99%
“…give compound 48 in good yield (81%). (13), yields of isolated products are presented in each case. b, The yield was calculated based on 1 HNMR of the isolated inseparable mixture of the desired product and (+)-drim-9(11)-en-8α-ol after chromatography.…”
Section: Combination Of Decarboxylative Borylation and Suzuki Couplinmentioning
confidence: 99%
See 1 more Smart Citation
“…In 2018, Wu and his coworkers reported the divergent synthesis of (+)-8-epipuupehedione [46]. Figure 13 shows the synthesis of 8-epi-puupehedione based on the Lewis acid catalyzed cyclization with sclareolide as starting material.…”
Section: Synthesis Of Puupehenol By Friedel-crafts Coupling Reactionmentioning
confidence: 99%