102794-92-3Relevant academic research and scientific papers
An enantiocontrolled synthesis of pyrrolizidines, (-)-platynecine and (-)-hadinecine
Kang, Sung Ho,Kim, Geun Tae,Yoo, Yong Sang
, p. 603 - 606 (1997)
Trisubstituted allylic alcohols 13 and 14 have been converted into a single isomeric trans-oxazoline 16 via an intramolecular iodoamidation of the corresponding trichloroacetimidates, which have been elaborated into (-)-platynecine 1 and(-)-hadinecine 2 via a common intermediate pyrrolizidine.
Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues
Yoshida, Masahito,Saito, Koya,Kato, Hikaru,Tsukamoto, Sachiko,Doi, Takayuki
supporting information, p. 5147 - 5150 (2018/03/26)
The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.
Stereoselective, Ag-Catalyzed Cyclizations to Access Polysubstituted Pyran Ring Systems: Synthesis of C1-C12 Subunit of Madeirolide A
Watanabe, Kazuhiro,Li, Jinming,Veerasamy, Nagarathanam,Ghosh, Ankan,Carter, Rich G.
supporting information, p. 1744 - 1747 (2016/05/19)
The exploration into the scope of a silver-catalyzed cyclization (AgCC) of propargyl benzoates for accessing pyran ring systems has been reported. The impact of the degree of substitution, nature of the substitution on the carbon backbone/benzoate moiety,
Exploiting hidden symmetry in natural products: Total syntheses of amphidinolides C and F
Mahapatra, Subham,Carter, Rich G.
supporting information, p. 10792 - 10803 (2013/08/23)
The total synthesis of amphidinolide C and a second-generation synthesis of amphidinolide F have been accomplished through the use of a common intermediate to access both the C1-C8 and the C18-C 25 sections. The development of a Ag-catalyzed cyclization of a propargyl benzoate diol is described to access both trans-tetrahydrofuran rings. The evolution of a Felkin-controlled, 2-lithio-1,3-dienyl addition strategy to incorporate C9-C11 diene as well as C8 stereocenter is detailed. Key controlling aspects in the sulfone alkylation/oxidative desulfurization to join the major subunits, including the exploration of the optimum masking group for the C18 carbonyl motif, are discussed. A Trost asymmetric alkynylation and a stereoselective cuprate addition to an alkynoate have been developed for the rapid construction of the C26-C34 subunit. A Tamura/Vedejs olefination to introduce the C26 side arm of amphidnolides C and F is employed. The late-stage incorporation of the C15, C18 diketone motif proved critical to the successful competition of the total syntheses.
ANTIBACTERIAL AGENTS
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Page/Page column 132, (2013/12/03)
Antibacterial compounds of formula (I) are provided, as well as stereoisomers and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.
Enantioselective total synthesis of amphidinolide F
Mahapatra, Subham,Carter, Rich G.
supporting information; experimental part, p. 7948 - 7951 (2012/09/08)
A common-intermediate approach is utilized in the total synthesis of amphidinolide F (see scheme, left) to access both the C1-C8 and the C18-C25 portions of the macrolide. A silver-catalyzed rearrangement/cyclization was employed to construct the two tetrahydrofuran rings. A Felkin-controlled, dienyl lithium addition to an α-chiral aldehyde incorporated both the C9-C11 diene and the alcohol at C8. An umpolung sulfone alkylation/oxidative desulfurization sequence is employed to couple the two moieties. Copyright
Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and δ-lactones
Sanchez-Sancho, Francisco,Valverde, Serafin,Herradon, Bernardo
, p. 3209 - 3246 (2007/10/03)
The syntheses of the chiral α,β-unsaturated lactones (+)-5, (-)-6, (+)-8, (+)-9, and (+)-10 have been efficiently achieved from readily available starting materials. The lactone (+)-5 has been synthesized in 7 steps from (R,R)-dimethyl tartrate (38-43% overall yield). The use of (+)-5 in formal syntheses of natural (+)-asperlin 4 and advanced intermediates for (+)-olguine 2 are also reported. The lactone (-)-6 has been prepared in 5 steps from (R)-malic and (44-50% overall yield). It can be a useful precursor for the syntheses of branched chain and deoxy nucleoside analogues. The preparation of (-)-6 constitutes formal syntheses of natural (+)-eldanolide 53 and the (+)-Geissman-Waiss lactone 54 (an intermediate for the syntheses of a variety of pyrrolizidine alkaloids). The lactones (+)-8, (+)-9 and (+)-10 have been synthesized from 3,4-di-O-acetyl-L-rhamnal 58. The highly diastereoselective transformations of (+)-9 and (+)-10, through sequential conjugate nucleophilic addition and enolate reaction, into densely functionalized chiral γ-lactones 12 are also reported. Copyright (C) Elsevier Science Ltd.
EFFICIENT SYNTHESIS OF (R)-5-(2-HYDROXYETHYL)-2(5H)-FURANONE FROM (R)-MALIC ACID
Herradon, Bernardo
, p. 191 - 194 (2007/10/02)
The title compound has been synthesized in five steps, 48percent overall yield, from (R)-malic acid.
Synthetic studies toward marine toxic polyethers. 4. Synthesis of segment-A of okadaic acid via anti-selectivity by heteroconjugate addition
Isobe,Ichikawa,Bai,Goto
, p. 5203 - 5206 (2007/10/02)
Segment-A of okadaic acid was synthesized in an optically active form by coupling the lithium acetylide (segment-A2) and the previously prepared segment-A1. The key step was the preparation of the anti-diastereoisomer for the C-12/13
