- 11-Step Total Synthesis of Pallambins C and D
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The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.
- Martinez, Luisruben P.,Umemiya, Shigenobu,Wengryniuk, Sarah E.,Baran, Phil S.
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supporting information
p. 7536 - 7539
(2016/07/06)
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- IMIDAZOPYRIDAZINE COMPOUNDS
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The present invention relates to novel substituted imidazo[1,2-b]pyridazine compounds of Formula (I): pharmaceutical compositions thereof, and the use such compounds as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric disorders and neurological diseases.
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Page/Page column 161-162
(2008/06/13)
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- Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran
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The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono-S-ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position α-relative to the substituent has allowed the regiospecific alkylation. It provides a straightforward approach to several 3-monothiosubstituted furans which are receiving increasing interest as odour and flavour chemicals.
- Alvarez-Ibarra, Carlos,Quiroga, Maria L.,Toledano, Emilio
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p. 4065 - 4078
(2007/10/03)
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- Structure-Odor Correlation, XXI. Olfactory Properties and Convenient Synthesis of Furans and Thiophenes Related to Rose Furan and Perillene and Their Isomers
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Starting from 3-bromofuran (1) or 3-bromothiophene (2) via alkylation in 2-position (-> 3-8) followed by the corresponding second alkylation in 3-position, we obtained rose furan (9), rose thiophene (10), and their analogs 11-16.From the α,β-unsaturated esters 17-20 by hydrogenation (-> 21-24), DIBAH reduction (-> 25-28), and Wittig reaction, perillene (29), thioperillene (30), and their analogs 29-36 were obtained.Olfactory evaluation showed that the difference between the furans and thiophene derivatives is remarkably small, particularly for perillene (29) compared with thioperillene (30), and their analogs.Also the influence of position and structure of the side chain is lower than expected within the compared compounds 9-36. - Keywords: Rose furan / Perillene / Furans / Thiophenes / Structure-odor correlation / Odoriferous substances
- Weyerstahl, Peter,Schenk, Anja,Marschall, Helga
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p. 1849 - 1854
(2007/10/03)
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- Preparation of 3-Bromo-2-methylfuran and 4-Bromo-2-methylfuran
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4-endo-5-exo-Dibromo-3-methyl-3,6-endo-oxyperhydrophthalic anhydride 3b and 4-exo-5-endo-dibromo-3-methyl-3,6-endo-oxyperhydrophthalic anhydride 3c were isolated from the bromo-adducts of 3-methyl-3,6-endo-oxy-1,2,3,6-tetrahydrophthalic anhydride 2.When 3b and 3c was heated in quinoline, only 3-bromo-2-methylfuran 4 was obtained from 3b and only 4-bromo-2-methylfuran 5 from 3c.
- Koyanagi, Jyunichi,Yamamoto, Katsumi,Nakayama, Kouji,Tanaka, Akira
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p. 1093 - 1096
(2007/10/02)
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