2013
DOI: 10.1002/asia.201301248
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Enantioselective Total Synthesis of Pinnaic Acid and Halichlorine

Abstract: The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation-… Show more

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Cited by 35 publications
(13 citation statements)
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“…Oxidation of allyl alcohol 19 with Dess–Martin periodinane afforded enone 20 , which was then subjected to Corey-Bakshi-Shibata reduction using ( R )-2-Me-CBS and borane dimethylsufide complex (BMS) affording segment 6a In excellent distereoselectivity (15:1 dr, by 1 H and 13 C NMR analysis). [18] Allylic alcohol 6a was obtained in 55% yield along with olefin-reduced by product. We also investigated this reaction using borane tetrahydrofuran complex or catecholborane instead of BMS, however, the yield was not improved.…”
Section: Resultsmentioning
confidence: 99%
“…Oxidation of allyl alcohol 19 with Dess–Martin periodinane afforded enone 20 , which was then subjected to Corey-Bakshi-Shibata reduction using ( R )-2-Me-CBS and borane dimethylsufide complex (BMS) affording segment 6a In excellent distereoselectivity (15:1 dr, by 1 H and 13 C NMR analysis). [18] Allylic alcohol 6a was obtained in 55% yield along with olefin-reduced by product. We also investigated this reaction using borane tetrahydrofuran complex or catecholborane instead of BMS, however, the yield was not improved.…”
Section: Resultsmentioning
confidence: 99%
“…Arimoto and co-workers reported a total synthesis of pinnaic acid and halichlorine using a one-pot, four-step hydrogenation-cyclization reaction for the stereoselective cyclization of the spirocyclopentane (Scheme 48). 60 The onepot reaction comprised reduction of the olefin, deprotec-…”
Section: Hydrogenation/deprotection/cyclization/ Trifluoroacetylationmentioning
confidence: 99%
“…RCM of 24 with the second-generation Grubbs catalyst was very sluggish even in refluxing toluene with additional catalyst loading. When conducted under reduced pressure (2.3 kPa, vacuum pump) in mesitylene, however, the RCM proceeded at an acceptable rate at 50 °C, furnishing 25 in 76% yield after 20 h of stirring . Tetrahydrofuran ring formation from 25 with triflic acid and subsequent dihydroxylation of the resulting tricycle 26 with OsO 4 afford vicinal diol 27 .…”
mentioning
confidence: 99%