89328-75-6Relevant academic research and scientific papers
Asymmetric synthesis of the four stereoisomers of 5-deoxystrigol
Lachia, Mathilde,Dakas, Pierre-Yves,De Mesmaeker, Alain
supporting information, p. 6577 - 6581 (2015/01/09)
Two approaches to the strigolactone tricyclic lactone skeleton 2 were investigated using ketene/ketene-iminium cycloaddition to olefins. Finally, the first enantioselective access to the four stereoisomers of 5-deoxystrigol 1 is reported using an intramolecular [2+2] cycloaddition of homochiral ketene-iminium salts 5. Very high asymmetric control was achieved with C-2 symmetric pyrrolidines as chiral auxiliary.
OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE
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Page/Page column 100, (2013/05/09)
Compounds are disclosed that are useful for treating ophthalmic conditions caused by or related to production of toxic visual cycle products that accumulate in the eye, such as dry adult macular degeneration, as well as conditions caused by or related to the misfolding of mutant opsin proteins and/or the mis-localization of opsin proteins. Compositions of these compounds alone or in combination with other therapeutic agents are also described, along with therapeutic methods of using such compounds and/or compositions. Methods of synthesizing such agents are also disclosed.
Synthesis and Biological Activity of 7'-, 8'-, and 9'-Alkyl Analogues of Abscisic Acid
Nakano, Sei-ichi,Todoroki, Yasushi,Hirai, Nobuhiro,Ohigashi, Hajime
, p. 1699 - 1706 (2007/10/02)
In order to examine the hypothesis of pseudo-symmetry in the abscisic acid (ABA) molecule, (+/-)-7'-,8'-, and 9'-methyl, and (+/-)-7'-, 8'-, and 9'-ethyl analogues of abscisic acid, whose pseudo-symmetry is decreased, weresynthesized and, after optical resolution, tested for their inhibitory activity in four bioassays.The correlation of the decrease in the activity of (-)-7'- and 9'-alkyl-ABAs with that of (+)-9'- and 7'-alkyl-ABAs, respectively, seemed to agree with the hypothesis.The decrease in activity by alkylating C-8' of (+)-ABA was smaller than that by alkylating C-7' and C-9' of (+)-ABA, indicating that the activity was relatively unaffected by the bulky group at C-8' of (+)-ABA.Alkylation of C-8' and C-9', especially that of C-8', of (-)-ABA markedly reduced the activity.If the high activity of unnatural (-)-ABA is attributable to the pseudo-symmetry of the molecule, C-8' of (-)-ABA would occupy the space facing the re-face of C-2' in natural (+)-ABA.The low activity of (-)-8'-alkyl-ABA suggests the presence of a strict steric requirement of the binding sites to occupy the re-face of C-2' in (+)-ABA.
A Novel Pentaannulation Sequence. Facile Access to Key Intermediates for the Synthesis of ExaltoneR and Muscone
Fehr, Charles
, p. 2519 - 2524 (2007/10/02)
Treatment of the sulfonyl ketones 1 a and 1 b with potassium t-butoxide in toluene or with potassium hydroxyde in toluene/dimethyl sulfoxide affords in high yield the bicyclic dienes 3 a and 3 b, importantbprecursors for exaltoneR and (+/-)-muscone.An Application of this novell pentaannulation sequence is demonstrated for the solfonyl ketones 6, 10, and 14.An intermolecular variant is exemplified by the synthesis of diene 22.
