54716-12-0Relevant academic research and scientific papers
Method for preparing Z-isomer by E-isomer of alpha, beta-nonsaturated carbonyl compound
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Paragraph 0056; 0057, (2017/04/29)
The invention provides a method for preparing a Z-isomer by an E-isomer of an alpha, beta-nonsaturated carbonyl compound. The method uses nitrogen-containing chiral binaphthol phosphoramidite to prepare a catalyst, under mild reaction condition, the E-isomer of the alpha, beta-nonsaturated carbonyl compound is efficiently conversed to the Z-isomer. The method is especially suitable for preparing neral through isomerization of partial geranial in a citral split residual material, the citral with mol ratio of the obtained geranial to neral being 1:1 can be reused for splitting the neral, raw material utilization rate is increased, and the cost is reduced.
Selective Oxidation of Benzylic and Allylic Alcohols Using Mn(OAc) 3/Catalytic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Cosner, Casey C.,Cabrera, Pablo J.,Byrd, Katherine M.,Adams Thomas, Asia M.,Helquist, Paul
supporting information; experimental part, p. 2071 - 2073 (2011/06/19)
A practical, chemoselective oxidation of alcohols employing catalytic quantities of DDQ as the oxidant and Mn(OAc)3 as the co-oxidant is described. Electron-rich benzylic alcohols are oxidized efficiently to their corresponding carbonyls, but less electron-rich benzylic alcohols remain unchanged. Allylic alcohols are rapidly oxidized to their corresponding aldehyde or ketone counterparts in high yields. This protocol is operationally simple, employs an inexpensive source of Mn(OAc)3, has short reaction times, and exhibits a significant chemoselectivity favoring allylic alcohols over benzylic alcohols. This procedure also avoids the use of very large excesses of reagents and sometimes poor reproducibility that characterize previously developed reagents such as MnO2
Total synthesis of cytostatin
Lawhorn, Brian G.,Boga, Sobhana B.,Wolkenberg, Scott E.,Boger, Dale L.
, p. 65 - 70 (2007/10/03)
The total synthesis of cytostatin, an antitumor agent belonging to the fostriecin family of natural products, is disclosed. The convergent route features a key epoxide opening reaction to join the two stereotriad units and a single-step late stage, stereo
Total synthesis and evaluation of cytostatin, its C10-C11 diastereomers, and additional key analogues: Impact on PP2A inhibition
Lawhorn, Brian G.,Boga, Sobhana B.,Wolkenberg, Scott E.,Colby, David A.,Gauss, Carla-Maria,Swingle, Mark R.,Amable, Lauren,Honkanen, Richard E.,Boger, Dale L.
, p. 16720 - 16732 (2007/10/03)
The total synthesis of cytostatin, an antitumor agent belonging to the fostriecin family of natural products, is described in full detail. The convergent approach relied on a key epoxide-opening reaction to join the two stereotriad units and a single-step
Pericyclic Reactions in Nature: Evidence for a Spontaneous -Hydrogen Shift and an 8?e Electrocyclic Ring Closure in the Biosynthesis of Olefinic Hydrocarbons from Marine Brown Algae (Phaeophyceae).
Pohnert, Georg,Boland, Wilhelm
, p. 10235 - 10244 (2007/10/02)
The stereochemistry of the algal C11H16 hydrocarbon giffordene 3 results from a spontaneous -sigmatropic hydrogen shift of the thermolabile (1,3Z,5Z,8Z)-undecatetraene 8.An 8?e electrocyclisation of (1,3Z,5Z,7E)-nonatetraene 9 is substantiated for the synthesis of 7-methylcyclooctatriene 5, a product of the Mediterranean brown alga Cutleria multifida.Low temperature syntheses (-30 deg C) of the thermolabile precursors 8 and 9 are described.The activation energies of the -sigmatropic hydrogen shift 8 -> 3 (Ea = 67.4 kJ mol-1) and of the 8?e electrocyclisation 9 -> 5 (Ea = 59.4 kJ mol-1) are the lowest values currently known for natural pericyclic reactions.
Stereoselective Synthesis of 2Z,4E-Dienals by Addition of Organometallic Reagents to Pyrylium Perchlorate
Furber, Mark,Herbert, John M.,Taylor, Richard J. K.
, p. 683 - 690 (2007/10/02)
A facile and stereoselective approach to 2Z,4E-dienals and derived products is presented.The method involves addition of an organometallic reagent to a pyrylium salt, followed by electrocyclic ring-opening of the intermediate 2H-pyran, to give the desired Z,E-dienal, usually with greater than 95percent stereochemical purity.These dienals may be trapped in situ with a second organometallic reagent, or oxidised or redused, without loss of stereochemical integrity.The synthesis of (1,3Z,5E)-undeca-1,3,5-triene, a component of the essential oils of the brown Hawaiian seaweeds Dictyopteris plagiogramma and D. australis, is reported to illustrate the simplicity of the procedure.
Stereospecific Synthesis of Dienes and Trienes from Pyrylium Perchlorate: a Convergent Approach to Leukotrienes
Furber, Mark,Taylor, Richard J. K.
, p. 782 - 783 (2007/10/02)
A range of conjugated dienes and trienes have been prepared in a stereospecific manner by the treatment of pyrylium perchlorate with organolithium reagents; model studies have been carried out which demonstrate the suitability of this methodology for the
