- A synthetic natural product Tarchonanthuslactone isomer of
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The invention provides a method for synthesizing a natural product Tarchonanthuslactone isomer. According to the method, methyl-3-hydroxybutyrate is used as a raw material, and PMB ester protection, LiALH4 reduction, Swern oxidation, Mukaiyama Aldol reaction, ester hydrolysis, Yanaguchi cyclization, de-protection and condensation are performed, so that the natural product Tarchonanthuslactone isomer is obtained. The synthetic route is novel and reasonable in design, the raw materials are cheap and easy to obtain, the operation process is simple and convenient, the reaction condition is mild, the rate is high, side reaction is less, the operation is simple and convenient, and the synthesizing cost is greatly reduced.
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- New method for asymmetrically synthesizing natural product (-)-Euscapholide isomer
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The invention relates to a new method for asymmetrically synthesizing a natural product (-)-Euscapholide isomer. The method comprises the following steps: carrying out methoxybenzyl group protection on (R)-3-hydroxymethyl butyrate used as an initial raw material, reducing by using diisobutylaluminium hydride, carrying out a Mukaiyama aldol reaction, reducing by using sodium borohydride, carrying out ring closure under acidic conditions, eliminating hydroxyl groups, and deprotecting to complete asymmetric total synthesis of the target molecule 1. The method has the advantages of novel and reasonable synthesis route design, cheap and easily available raw material, simple operating process, mild reaction conditions, efficient completion of the asymmetric total synthesis of the Euscapholide isomer with two chiral centers, and single product configuration.
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- Total Synthesis of (+)-7-epi-Tarchonanthuslactone via a Chelation-Controlled Mukaiyama Aldol Reaction
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An asymmetric total synthesis of (+)-7-epi-tarchonanthuslactone was achieved from commercially available methyl (R)-3-hydroxybutyrate. The key step employed a diastereoselective chelation-controlled Mukaiyama aldol reaction to construct the chiral hydroxyl group at the C-5 position.
- Huang, Shuangping,Liu, Dongwang,Tang, Linjun,Huang, Fei Fei,Zhang, Jianting,Wang, Xiaoji
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supporting information
p. 1240 - 1247
(2015/03/30)
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- Stereoselective synthesis of macrosphelide i
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An efficient total synthesis of macrosphelide I, has been achieved starting from commercially available chiral materials, ethyl (S)-lactate and methyl (R)-3-hydroxybutyrate. Titanium(IV) promoted the regioselective nucleophilic opening reaction of epoxy a
- Veena, Bacchu,Sharma, Gangavaram V. M.
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supporting information
p. 2039 - 2043
(2014/11/08)
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- Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin
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The resorcylic acid lactones (RAL) are endowed with diverse biological activity ranging from transcription factor modulators (zearalenone and zearalenol) to HSP90 inhibitors (radicicol and pochonin D) and reversible (aigialomycin D) as well as irreversibl
- Dakas, Pierre-Yves,Jogireddy, Rajamalleswaramma,Valot, Gaelle,Barluenga, Sofia,Winssinger, Nicolas
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supporting information; experimental part
p. 11490 - 11497
(2010/04/28)
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- A Combinatorial Synthesis of a Macrosphelide Library Utilizing a Palladium-Catalyzed Carbonylation on a Polymer Support
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Supported total synthesis: The combinatorial synthesis of a 122-membered macrosphelide library including macrosphelides A, C, E, and F (see picture) has been achieved based on a unique strategy for a three-component coupling utilizing a palladium-catalyzed chemoselective carbonylation and an unprecedented macrolactonization on a polymer support.
- Takahashi, Takashi,Kusaka, Shin-Ichi,Doi, Takayuki,Sunazuka, Toshiaki,Omura, Satoshi
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p. 5230 - 5234
(2007/10/03)
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- Studies on the total synthesis of macrolactin A. A stereoselective synthesis of the C3-C13 and C14-C24 fragments
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Synthetic studies towards the C3-C13 (2) and C14-C24 (3) segments of the potent antiviral and antitumor compound macrolactin A (1) are presented. Segment 2 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E,Z-diene-moiety. Segment 3 was obtained from the chiral pool derived sulfone 4 via an α- alkylation-desulfonation reaction sequence. (C) 2000 Elsevier Science Ltd.
- Li, Shukun,Xu, Rui,Bai, Donglu
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p. 3463 - 3466
(2007/10/03)
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- Synthesis of tuckolide, a new cholesterol biosynthesis inhibitor
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Tuckolide (decarestrictine D), a 10-membered lactone isolated from P. corylophilum and polyporus tuberaster fungi that potently inhibits cholesterol biosynthesis, was synthesized. The key steps include a Sharpless catalytic asymmetric dihydroxylation reaction (AD) of the methoxymethyl (MOM) ether protected diene 2 and a direct Corey-Nicolaou lactonization reaction of seco-acid 1 with added silver perchlorate. The selectivity of the dihydroxylation step was found to be highly dependent on the nature of the protecting group adjacent to the diene in 2. The selectivity of the asymmetric dihydroxylation reaction of 2 indicates that both steric and electronic effects can lead to significant amounts of the undesired isomers. This synthesis establishes the absolute stereochemistry of tuckolide showing the C3 hydroxyl bearing carbon with an S-configuration comparable in an absolute sense to that in the lactone portion of the HMG-CoA reductase inhibitor compactin.
- Andrus, Merritt B.,Shih, Tzenge-Lien
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p. 8780 - 8785
(2007/10/03)
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