16666-78-7Relevant articles and documents
Synthesis of 2- and 17-substituted estrone analogs and their antiproliferative structure-activity relationships compared to 2-methoxyestradiol
Shah, Jamshed H.,Agoston, Gregory E.,Suwandi, Lita,Hunsucker, Kimberly,Pribluda, Victor,Zhan, Xiaoguo H.,Swartz, Glenn M.,LaVallee, Theresa M.,Treston, Anthony M.
, p. 7344 - 7352 (2009)
A novel series of 17-modified and 2,17-modified analogs of 2-methoxyestradiol (2ME2) were synthesized and characterized. These analogs were designed to retain or potentiate the biological activities of 2ME2 and have diminished metabolic liability. The ana
A general strategy for the stereocontrolled preparation of diverse 8- and 9-membered Laurencia -type bromoethers
Snyder, Scott A.,Treitler, Daniel S.,Brucks, Alexandria P.,Sattler, Wesley
, p. 15898 - 15901 (2011)
A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.
Synthetic and Spectroscopic Investigations Enabled by Modular Synthesis of Molecular Phosphaalkyne Precursors
Transue, Wesley J.,Yang, Junyu,Nava, Matthew,Sergeyev, Ivan V.,Barnum, Timothy J.,McCarthy, Michael C.,Cummins, Christopher C.
supporting information, p. 17985 - 17991 (2019/01/09)
A series of dibenzo-7-phosphanorbornadiene compounds, Ph3PC(R)PA (1-R; A = C14H10, anthracene; R = Me, Et, iPr, sBu), are reported to be capable of thermal fragmentation to generate alkyl-substituted phosphaalkynes (RC≡P) concomitant with triphenylphosphine and anthracene. Facile preparation of these molecular precursors proceeds by treatment of ClPA with the appropriate ylide Ph3P=CHR (2 equiv). For methyl, ethyl, and isopropyl substituents, the phosphaalkyne conversions are measured to be 56-73% in solution by quantitative 31P NMR spectroscopy. In the case of compound 1-Me, the kinetic profile of its spontaneous unimolecular fragmentation is investigated by an Eyring analysis. The resulting 1-phosphapropyne is directly detected by solution NMR spectroscopy and gas phase rotational microwave spectroscopy. The latter technique allows for the first time measurement of the phosphorus-31 nuclear spin-rotation coupling tensor. The nuclear spin-rotation coupling provides a link between rotational and NMR spectroscopies, and is contextualized in relation to the chemical shift anisotropy.
Olefin metathesis based approach to diversely functionalized pyrrolizidines and indolizidines; total synthesis of (+)-monomorine
Lesma, Giordano,Colombo, Alessia,Sacchetti, Alessandro,Silvani, Alessandra
experimental part, p. 590 - 596 (2009/06/20)
New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolidines were synthesized from the cross and ring-closing metathesis reactions of appropriate intermediates, readily available from L-pyroglutamic acid. The versatility of this strategy was demonstrated by the synthesis of an indolizidine-based azasugar analogue and of the natural alkaloid (+)-monomorine.
