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Reiko Abe

Bio: Reiko Abe is an academic researcher from Hokkaido University. The author has contributed to research in topics: Catalysis & Protecting group. The author has an hindex of 2, co-authored 4 publications receiving 253 citations.

Papers
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Journal ArticleDOI
TL;DR: In this paper, a mild protection method for hydroxy functions with a MPM (4methoxybenzyl) group, various types of hydroxy compounds were treated with MPM trichloroacetimidate in the presence of an acid catalyst.

216 citations

Journal ArticleDOI
TL;DR: In this article, new protecting groups for the hydroxy function, 3-methoxybenzyl (3-MPM) and 3, 5-dimethoxy benzyl(3-5-DMPM) groups are slowly removed by DDQ oxidation at room temperature.
Abstract: New protecting groups for the hydroxy function, 3-methoxybenzyl (3-MPM) and 3, 5-dimethoxybenzyl (3, 5-DMPM) groups are slowly removed by DDQ oxidation at room temperature and distinguished from readily removable 4-methoxybenzyl (MPM). They are stable to strong acids.

37 citations

Journal ArticleDOI
TL;DR: In this paper, a mild protection method for hydroxy functions with a MPM (4methoxybenzyl) group, various types of hydroxy compounds were treated with MPM trichloroacetimidate in the presence of an acid catalyst.
Abstract: In order to establish a mild protection method for hydroxy functions with a MPM (4-methoxybenzyl) group, various types of hydroxy compounds were treated with MPM trichloroacetimidate in the presence of an acid catalyst. A catalytic amount (0.3 mol %) of trifluoromethanesulfonic acid was most effective and the reaction was completed within 40 min at room temperature even for highly sterically hindered hydroxy groups.

3 citations

Journal ArticleDOI
TL;DR: In this paper, new protecting groups for the hydroxy function, 3-methoxybenzyl (3-MPM) and 3, 5-dimethoxy benzyl(3-5-DMPM) groups are slowly removed by DDQ oxidation at room temperature.
Abstract: New protecting groups for the hydroxy function, 3-methoxybenzyl (3-MPM) and 3, 5-dimethoxybenzyl (3, 5-DMPM) groups are slowly removed by DDQ oxidation at room temperature and distinguished from readily removable 4-methoxybenzyl (MPM). They are stable to strong acids.

Cited by
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Journal ArticleDOI
TL;DR: This data indicates that the phytochemical properties of Aplysiatoxin-like substances have changed significantly since their discovery in the 1970s, and these changes have implications for the design of new drugs and their application in medicine.
Abstract: 1. Intoduction 4348 2. Oxolane Macrodiolides 4348 2.1. Pamamycin 607 (1) 4348 2.1.1. Thomas Total Synthesis20 4349 2.1.2. Lee Total Synthesis28 4351 2.1.3. Metz Total Synthesis35 4353 2.1.4. Kang Total Synthesis41 4354 2.2. Amphidinolide X (2) 4356 2.2.1. Fürstner Total Synthesis59 4356 3. Oxane/Oxene Macrodiolides 4359 3.1. SCH 351448 (3) 4359 3.1.1. Lee Total Synthesis71 4359 3.2. Swinholide A (4) 4360 3.2.1. Paterson Total Synthesis82 4360 3.2.2. Nicolaou Total Synthesis83 4360 4. Cyclic Acetal Macrodiolides 4362 4.1. Cycloviracin B1 (5) 4362 4.1.1. Fürstner Total Synthesis96 4363 4.2. Glucolipsin A (6) 4366 4.2.1. Fürstner Total Synthesis117 4366 5. Cyclic Hemiketal Macrodiolides 4368 5.1. Boromycin (7) 4368 5.1.1. White Total Synthesis123 4368 5.2. Tartrolon B (8) 4369 5.2.1. Mulzer Total Synthesis130 4370 5.3. Debromoaplysiatoxin (9) and Aplysiatoxin (10) 4373 5.3.1. Kishi Total Synthesis142 4373 6. Conclusions 4375 7. Acknowledgments 4375 8. References 4375

256 citations

Journal ArticleDOI
TL;DR: In the presence of a catalytic amount of triphenylphosphine, methyl 2,3-butadienoate smoothly reacted with aromatic or heteroaromatic N -tosylimines at room temperature to afford the [3+2] cycloaddition product in excellent yield as mentioned in this paper.

227 citations

Journal ArticleDOI
TL;DR: An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale.
Abstract: An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) σ-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphonium salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.

220 citations

Journal ArticleDOI
TL;DR: In this paper, a practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence).
Abstract: A practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence). The absolute stereochemistry of the C(1)-C(6) (7), C(9)-C(16) (8), and C(17)-C(24) (9) subunits was established via substrate-controlled, boron-mediated, aldol reactions of the chiral ethyl ketones 10, 11, and 12. Key fragment coupling reactions were a lithium-mediated, anti-selective, aldol reaction of aryl ester 8 (under Felkin-Anh induction from the aldehyde component 9), followed by in situ reduction to produce the 1,3-diol 40, and a (+)-diisopinocampheylboron chloride-mediated aldol reaction of methyl ketone 7 (overturning the inherent substrate induction from the aldehyde component 52) to give the (7S)-adduct 58. The flexibility of our overall strategy is illustrated by the synthesis of a number of diastereomers and structural analogues of discodermolide, which should serve as valuable probes for structure-activity studies.

193 citations

Journal ArticleDOI
TL;DR: The research reported herein represents an important step toward the preparation of functional mesostructures with controlled helical architectures and shows the benefits of reducing the nonfunctional part of the molecule, in this case with short chiral isopentyl chains.
Abstract: The controlled preparation of chiral structures is a contemporary challenge for supramolecular science because of the interesting properties that can arise from the resulting materials, and here we show that a synthetic nonamphiphilic C3 compound containing π-functional tetrathiafulvalene units can form this kind of object. We describe the synthesis, characterization, and self-assembly properties in solution and in the solid state of the enantiopure materials. Circular dichroism (CD) measurements show optical activity resulting from the presence of twisted stacks of preferential helicity and also reveal the critical importance of fiber nucleation in their formation. Molecular mechanics (MM) and molecular dynamics (MD) simulations combined with CD theoretical calculations demonstrate that the (S) enantiomer provides the (M) helix, which is more stable than the (P) helix for this enantiomer. This relationship is for the first time established in this family of C3 symmetric compounds. In addition, we show th...

140 citations