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Cacbohyđrate synthesis, functionaliation, applications

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Cacbohyđrate synthesis, functionaliation, applications

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications Wilkes UniversityKuniaki Tatsuta, Editor Waseda UniversityLibrary of Congress Cataloging-in-Publication DataCarbohydrate synthons in natural products

chemistry : synthesis, functionalization, and applications / Zbigniew J. Witczak, editor, Kuniaki Tatsuta, editor.p. cm.—(ACS symposium scries ; 841)“ Cacbohyđrate synthesis, functionaliation, applications

218th National Meeting of the American Chemical Society, San Francisco, California, March 26-30, 2000.”Includes bibliographical references and indexes

Cacbohyđrate synthesis, functionaliation, applications

.ISBN 0-8412-3740-91. Carbohydrates—Congresses. 2. Organic compounds—Synthesis—Congresses. 3. Ch i rality—Congresses.I. Witczak, Zbigniew J., 1947- II

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications an Francisco, Calif.). V. Series.QD320 C39 2002547' 78—dc212002028371The paper used in this publication meets the minimum requirements of American Nat

ional Standard for Information Sciences—Permanence of Paper for Printed Library Materials, ANSI Z39.48-1984.Copyright © 2003 American Chemical Society Cacbohyđrate synthesis, functionaliation, applications

Distributed by Oxford University PressAll Rights Reserved. Reprographic copying beyond that permitted by Sections 107 or 108 of the U.S. Copyright Act

Cacbohyđrate synthesis, functionaliation, applications

is allowed for internal use only, provided that a pcr-chapter fee of $22.50 plus $0.75 per page is paid to the Copyright Clearance Center, Inc., 222

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications these and other permission requests to ACS Copyright Office, Publications Division, 1155 16th St., N.W., Washington, DC 20036.The citation of trade na

mes and/or names of manufacturers in this publication is not to be construed as an endorsement or as approval by ACS of the commercial products or ser Cacbohyđrate synthesis, functionaliation, applications

vices referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license

Cacbohyđrate synthesis, functionaliation, applications

or as a conveyance of any right or permission to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any p

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications ut specific indication thereof, are not to be considered unprotected by law.DDFMTcn IXT TUC I rxiF'TC'n QTATCC A UCDir AForewordThe ACS Symposium Seri

es was first published in 1974 to provide a mechanism for publishing symposia quickly in book form. The purpose of the series is to publish timely, co Cacbohyđrate synthesis, functionaliation, applications

mprehensive books developed from ACS sponsored symposia based on current scientific research. Occasionally, books are developed from symposia sponsore

Cacbohyđrate synthesis, functionaliation, applications

d by other organizations when the topic is of keen interest to the chemistry' audience.Before agreeing to publish a book, the proposed table of conten

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications rs may be added to provide comprehensiveness. When appropriate, overview or introductory chapters are added. Drafts of chapters are peer-reviewed prio

r to final acceptance or rejection, and manuscripts are prepared in camera-ready format.As a rule, only original research papers and original review p Cacbohyđrate synthesis, functionaliation, applications

apers are included in the volumes. Verbatim reproductions of previously published papers are not accepted.ACS Books DepartmentPrefaceThe synthesis of

Cacbohyđrate synthesis, functionaliation, applications

new chiral organic compounds and the improved synthesis of known substances will always be a major task for the professional chemist. When constructin

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications ks as an alternative approach.Carbohydrates represent a unique family of polyfunctional compounds, which can be chemically or enzymatically manipulate

d in a multitude of ways. Carbohydrates have been extensively used as starting materials in enantioselective synthesis of many, complex natural produc Cacbohyđrate synthesis, functionaliation, applications

ts with multiple chirality centers. Synthetic organic chemistry that utilizes these carbohydrate building blocks continues to spawn revolutionary disc

Cacbohyđrate synthesis, functionaliation, applications

overies in medicinal chemistry, pharmacology, molecular biology, glycobiology, and medicine simply by providing not only the raw material but also the

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications the core of synthetic carbohydrate chemistry. The environmentally and ecologically friendly nature of carbohydrates is also a cornerstone in their fut

ure developments in the polymer and pharmaceutical industries and in the area of carbohydrate therapeutics in particular.Corey (E.J Corey Pure Appl Ch Cacbohyđrate synthesis, functionaliation, applications

etn 1969,14, 30) introduced the term synthon in 1969 when he published his innovative strategies for the construction of complex molecules by consider

Cacbohyđrate synthesis, functionaliation, applications

ing a retrosynthetic analysis. Later on, Hanessian’s (Total Synthesis of Natural Products: The ‘Chiron'Approach; Pergamon Press, 1983) introduction in

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications al products.Despite the greater awareness of carbohydrate synthons in recent years, the full potential of the carbohydrate chiral pool is still notful

ly used. Thus, this fact gives enormous rationale in organizing our symposium and presenting new developments by a team of world-class scientists. Con Cacbohyđrate synthesis, functionaliation, applications

sequently, publishing this symposium proceeding will assist the carbohydrate community in keeping abreast of new innovations. We hope that these few,

Cacbohyđrate synthesis, functionaliation, applications

important forward-looking topics of brand new developments from world-class leading laboratories will effectively fill the gap of previously unavailab

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications cks, L-arabinose is one of the most important and easily commercially available monosaccharides. Next, in terms of availability and potential function

ality are naturally protected 1,6-anhydrosugars derivatives such as levoglucosan and levoglucosenone. Both compounds possess enormous potential for be Cacbohyđrate synthesis, functionaliation, applications

coming new stars among industrial chemicals, simply because of their multiple usage in many areas of industry (including polymer chemistry, biotechnol

Cacbohyđrate synthesis, functionaliation, applications

ogy, pharmaceutical intermediates, and carbohydrate scaffolds for combinatorial chemistry approaches). Industrial production of these convenient chira

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications d as green chemistry. The raw carbohydrate material for the functionalization into useful building blocks must be economically feasible and cost effec

tive; waste cellulosic materials fit into that category very well. Particularly valuable building blocks such as levoglucosenone, isolevoglucosenone, Cacbohyđrate synthesis, functionaliation, applications

L-arabinose, parasorbic acid, dihydropyranones, 3-hydroxy-y-butyro-lactones, 1 -thio-1,2-ớ-isopropylidene acetals, co-bromo-a-p unsaturated aldonolact

Cacbohyđrate synthesis, functionaliation, applications

ones, bicyclic furanones, arabinonic acid y-lac-one and glycosyl isocyanides are explored for their synthetic applicability in many synthetic targets

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

Cacbohyđrate synthesis, functionaliation, applications the 218th ACS National Meeting in San Francisco, California on March 26-30, 2000. Other chapters, not presented at the symposium, are contributions fr

om leading scientists in the field of carbohydrate chemistry. Cacbohyđrate synthesis, functionaliation, applications

ACS SYMPOSIUM SERIES 841Carbohydrate Synthons in Natural Products ChemistrySynthesis, Functionalization, and ApplicationsZbigniew J. Witczak, Editor W

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