- Bacilosarcins A and B, novel bioactive isocoumarins with unusual heterocyclic cores from the marine-derived bacterium Bacillus subtilis
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Two novel isocoumarins, bacilosarcins A (1) and B (2) were isolated from a culture broth of the marine-derived bacterium Bacillus subtilis TP-B0611. The structures and absolute configurations of 1 and 2 were determined on the basis of spectroscopic analyses and chemical conversions. Compound 1 possesses an unprecedented 3-oxa-6,9-diazabicyclo[3.3.1]nonane ring system while 2 has a 2-hydroxymorpholine moiety that is rare in nature. These compounds showed growth inhibition against barnyard millet.
- Azumi, Miwa,Ogawa, Ken-ichi,Fujita, Tsuyoshi,Takeshita, Michinori,Yoshida, Ryuji,Furumai, Tamotsu,Igarashi, Yasuhiro
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- Application of Pd-Catalyzed C-H Alkylation Reaction in Total Syntheses of Twelve Amicoumacin-Type Natural Products
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Enantioselective total syntheses of 12 amicoumacin-type natural products are accomplished with a palladium(II)-catalyzed C-H alkylation as the key step to furnish the 3,4-dihydroisocoumarin scaffold. The target chemicals are assembled in a convergent prot
- Wang, Hui-Hong,Li, Zhao,Feng, Yi-Yue,Yin, Gao-Feng,Shi, Tao,He, Dian,Wang, Xiao-Dong,Wang, Zhen
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supporting information
p. 6956 - 6960
(2021/09/11)
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- Total Synthesis of Originally Proposed and Revised Structure of Hetiamacin A
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The first total synthesis of the originally proposed and correct structures of hetiamacin A has been accomplished via Wittig olefination and Sharpless asymmetric dihydroxylation reaction. These total syntheses culminated in the stereostructural confirmati
- Wu, Gang,Liu, Shaowei,Wang, Ting,Jiang, Zhongke,Lv, Kai,Wang, Yucheng,Sun, Chenghang
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supporting information
p. 3566 - 3569
(2018/06/26)
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- Total synthesis of bacilosarcins A and B
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(Chemical Equation Presented) I want to ride my bicycle: The thermodynamic stability of nitrogen-containing heterocyclic ring systems is exploited in the first enantioselective total synthesis of bacilosarcins A and B, which has been achieved in simple tw
- Enomoto, Masaru,Kuwahara, Shigefumi
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supporting information; experimental part
p. 1144 - 1148
(2009/06/19)
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- Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.
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[structure: see text]. An efficient and highly stereoselective synthesis of the gastroprotective natural product AI-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldo
- Ghosh,Bischoff,Cappiello
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p. 2677 - 2680
(2007/10/03)
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- Total synthesis of AI-77-B: Stereoselective hydroxylation of 4-alkenylazetidinones
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A stereoselective synthesis of the anti-ulcer compound AI-77-B 1 is described. The 4-formylazetidinone 6 was converted into the 4-(Z)-alkene 23 using a phosphonate condensation, and dihydroxylation using osmium tetroxide and N-methylmorpholine W-oxide gav
- Broady, Simon D.,Rexhausen, Jost E.,Thomas, Eric J.
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p. 1083 - 1094
(2007/10/03)
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- A new enantioselective total synthesis of Al-77-B
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(formula presented) An enantioselective total synthesis of Al-77-B (1), a gastroprotective substance isolated from a culture broth of Bacillus pumilus Al-77, was performed in high overall yield. In this synthesis, the dihydroisocoumarin part 14 and the di
- Kotsuki, Hiyoshizo,Araki, Tomohiro,Miyazaki, Aya,Iwasaki, Mitsuhiro,Datta, Probal K.
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p. 499 - 502
(2008/02/11)
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- A Total Synthesis of the Natural Enantiomer of the Gastroprotective Natural Products AI-77-B and Amicoumacin C hydrochloride
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A total synthesis of the natural enantiomer of AI-77-B and amicoumacin C hydrochloride is described.
- Ward, Richard A.,Procter, Garry
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p. 12301 - 12318
(2007/10/02)
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- A Total Synthesis of AI-77-B
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A short total synthesis of AI-77-B (1) is reported, which produces the natural enantiomer using S-leucine and S-aspartic acid as the optically active starting materials. Key words: Natural product; AI-77-B; gastroprotective; total synthesis; enantioselect
- Ward, Richard A.,Procter, Garry
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p. 3359 - 3362
(2007/10/02)
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- Efficient total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77
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First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2·HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).
- Hamada,Hara,Kawai,Kohno,Shioiri
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p. 8635 - 8652
(2007/10/02)
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- Total Synthesis of Al-77-B
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Stereoselective hydroxylation of the β-lactam ester 8 is a key step in a total synthesis of Al-77-B 1.
- Broady, Simon D.,Rexhausen, Jost E.,Thomas, Eric J.
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p. 708 - 710
(2007/10/02)
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- STUDIES ON AI-77s, MICROBIAL PRODUCTS WITH GASTROPROTECTIVE ACTIVITY. STRUCTURES AND THE CHEMICAL NATURE OF AI-77s
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The structures and chemical nature of a novel gastroprotective substance AI-77-B (1) and its analogues AI-77-C (2), D (3), F (4) and G (5), which are produced by Bacillus pumilus AI-77, are described.The structure of 1 was confirmed to be 6-amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-aminohexanoic acid by X-ray in combination with chemical studies and the structures of 2, 3, 4 and 5 were determined by chemical syntheses from 1 and spectral analyses.
- Shimojima, Yukiji,Hayashi, Hiroshi,Ooka, Tadaaki,Shibukawa, Mitsuru,Iitaka, Yoichi
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p. 2519 - 2528
(2007/10/02)
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