Prostaglandins and congeners. 20. Synthesis of prostaglandins via conjugate addition of lithium trans-1-alkenyltrialkylalanate reagents. A novel reagent for conjugate 1,4-additions

Determination of the Absolute Configuration of (+)-2,7(14),10-Bisabolatrien- 1-ol-4-one from Japanese Cedar,Cryptomeria japonica

“…5 (2.66 g, 11.6 mmol) was reduced by LiAlH4 to give (4R)-10-bromo-1(6),8-pmenthadien-2-ol (2.54 g) according to the established procedure, 7) the hydroxyl group of the product (693 mg) then being protected as a THP ether (740 mg). 8) A solution of 3-bromo-2-methyl-2-butene (745 mg, 5 mmol) in dry THF (9 ml) was slowly added over 10 min to magnesium (375 mg) while stirring and keeping at "259 C under N2 gas. After terminating the exothermic reaction, the reactant was added to dry THF (6 ml) containing the THP ether (472 mg) and cuprous bromide (30 mg) while stirring for 30 min at "259 C. The solution was diluted with saturated ammonium chloride water and then extracted with diethyl ether.…”

“…After protecting the hydroxyl group as a THP ether, 8) (4R)-10-bromo-2-(tetrahydropyran-2-yloxy)-1(6),8-p-menthadiene was reacted with 3-methyl-2-butenylmagnesium bromide to produce (5R)-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)-3-(tetrahydropyran-2-yloxy)cyclohexene. After eliminating the THP, 9) (5R)-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)-2-cyclohexenol was oxidized with PDC to give (R)-cryptomerione (6).…”

Trends to Acid-Labile Cys Protecting Groups: Thp as an Efficient and Non-Aromatic Cys Protecting Group for Fmoc Chemistry

“…Apart of its recent application in Fmoc chemistry [26], Thp is extensively used as hydroxyl protecting group [27][28][29][30] as well as a linker [31][32][33][34], due to its chemical properties and its stability in strong bases, and acylating and alkylating agents among others. Accordingly, Thp is an excellent candidate for use in SPPS, but it is known that the main drawback should be the formation of a new stereocenter that leads to diastereomeric mixtures.…”

Peptides 2015, Proceedings of the 24th American Peptide Symposium

“…Moreover, Dtsamino acids are desulfurized to N-carboxyanhydrides (NCA's), and Dts-dipeptides give rise to hydantoins, all under unusually mild conditions [20,21].  Focusing on the trivalent phosphorus that can act to desulfurize Dts (and a related compound we call "EDITH"), this chemistry serves as an excellent entry to phosphorothioate DNA and RNA for "anti-sense" applications [27,28].  Lastly, Dts chemistry makes it possible to come up with a vastly milder variation to the classic Gabriel synthesis that converts alkyl halides to the corresponding amines -I particularly want to call attention to Mark Wood and collaborators for independent results in this direction [29].…”