Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis
作者： Kenshu Fujiwara , Keita Tanaka , Yasushi Katagiri , Hidetoshi Kawai , Takanori Suzuki
DOI: 10.1016/J.TETLET.2010.06.103
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摘要: Abstract Armatol F, isolated from the red alga Chondria armata as a polyether triterpene, has fused tricyclic ether moiety (BCD-ring) with an unusual cis ring junction at C18–C19 between C- and D-rings. En route to total synthesis of armatol stereoselective construction C18 C19 stereocenters by Ireland-Claisen rearrangement formation C-ring relay ring-closing olefin metathesis were established through monocyclic (C-ring) bicyclic (BC-ring) model compounds.
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sci-hub.se 参考文章(29)
R J Auchus, D F Covey, V Bork, J Schaefer, Solid-state NMR observation of cysteine and lysine Michael adducts of inactivated estradiol dehydrogenase. Journal of Biological Chemistry. ,vol. 263, pp. 11640- 11645 ,(1988) , 10.1016/S0021-9258(18)37832-3
Matthias Scholl, Sheng Ding, Choon Woo Lee, Robert H. Grubbs, Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Organic Letters. ,vol. 1, pp. 953- 956 ,(1999) , 10.1021/OL990909Q
Alessandro Dondoni, Giancarlo Fantin, Marco Fogagnolo, Alessandro Medici, Paola Pedrini, Hydroxy group inversion in thiazole polyols by an oxidation-reduction sequence. An entry to syn 1,2-diol fragments in masked carbohydrates The Journal of Organic Chemistry. ,vol. 54, pp. 702- 706 ,(1989) , 10.1021/JO00264A036
Jesse D. More, Nathaniel S. Finney, A simple and advantageous protocol for the oxidation of alcohols with O-iodoxybenzoic acid (IBX). Organic Letters. ,vol. 4, pp. 3001- 3003 ,(2002) , 10.1021/OL026427N
Takashi Yamanoi, Takashi Akiyama, Eiichi Ishida, Hiroyuki Abe, Masahide Amemiya, Toshiyuki Inazu, Horner-Wittig Reaction of Dimethyl 2,3-O-Isopropylidene-D-glyceroylmethylphosphonate and Its Application to the Formal Synthesis of D-erythro-C18-Sphingosine Chemistry Letters. ,vol. 18, pp. 335- 336 ,(1989) , 10.1246/CL.1989.335
Akiyoshi Goto, Kenshu Fujiwara, Ayako Kawai, Hidetoshi Kawai, Takanori Suzuki, Synthesis of the EF-Ring of Ciguatoxin 3C Based on the [2,3]-Wittig Rearrangement and Ring-Closing Olefin Metathesis Organic Letters. ,vol. 9, pp. 5373- 5376 ,(2007) , 10.1021/OL702231J
William R. Baker, Anthony K. L. Fung, Hollis D. Kleinert, Herman H. Stein, Jacob J. Plattner, Yoek Lin Armiger, Stephen L. Condon, Jerome Cohen, David A. Egan, Nonpeptide renin inhibitors employing a novel 3-aza(or oxa)-2,4-dialkyl glutaric acid moiety as a P2/P3 amide bond replacement. Journal of Medicinal Chemistry. ,vol. 35, pp. 1722- 1734 ,(1992) , 10.1021/JM00088A006
Thomas R. Hoye, Christopher S. Jeffrey, Manomi A. Tennakoon, Jizhou Wang, Hongyu Zhao, Relay Ring-Closing Metathesis (RRCM): A Strategy for Directing Metal Movement Throughout Olefin Metathesis Sequences Journal of the American Chemical Society. ,vol. 126, pp. 10210- 10211 ,(2004) , 10.1021/JA046385T
M.Letizia Ciavatta, Solimabi Wahidulla, Lisette D'Souza, Gennaro Scognamiglio, Guido Cimino, New bromotriterpene polyethers from the Indian alga Chondria armata Tetrahedron. ,vol. 57, pp. 617- 623 ,(2001) , 10.1016/S0040-4020(00)01031-0
Andre L. Gemal, Jean Louis Luche, Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects Journal of the American Chemical Society. ,vol. 103, pp. 5454- 5459 ,(1981) , 10.1021/JA00408A029