A Wandering Natural Products Chemist 0841217750, 0841218013

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A Wandering Natural Proa Chemist Koji Nakanish i.

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PROFILES, PATHWAYS, At ID I IREAM

Jeffrey I. Seeman, Series Editor

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A Wandering Natural Products Chemist

A Wandering Natural Products Chemist Koji Nakanishi

PROFILES, PATHWAYS, AND DREAMS Autobiographies of Eminent Chemists Jeffrey I. Seeman, Series Editor

American Chemical Society, Washington, DC 1991

1991 ACS Books Advisory Board Library of Congress Cataloging-in-Publication Data Nakanishi, Koji, 1925— A wandering natural products chemist / Koji Nakanishi. p.

cm.—(Profiles, pathways, and dreams, 1047-8329)

V. Dean Adams

Bonnie Lawlor

Tennessee Technological

Institute for Scientific Information

University

Includes bibliographical references and index.

John L. Massingill Paul S. Anderson

Dow Chemical Company

1. Nakanishi, Koji, 1925— . 2. ChemistsJapan—Biography. 3. Chemistry, Organic— History—20th century. I. Title. II. Series.

Merck Sharp & Dohme Research Laboratories

Robert McGorrin

QD22.N24A3 1990 [B]

Alexis T. Bell

ISBN 0-8412-1775-0.—ISBN 0-8412-1801-3 (pbk.)

540'.92—dc20

Kraft General Foods 90-45062 CIP

Jeffrey I. Seeman, Series Editor The paper used in this publication meets the minimum requirements of American National Standard for Information Sciences—Permanence of Paper for Printed Library Materials, ANSI Z39.48-1984.

®

Copyright © 1991 American Chemical Society All Rights Reserved. The copyright owner consents that reprographic copies may be made for personal or internal use or for the personal or internal use of specific clients. This consent is given on the condition, however, that the copier pay the stated per-copy fee through the Copyright Clearance Center, Inc., 27 Congress Street, Salem, MA 01970, for copying beyond that permitted by Sections 107 or 108 of the U.S. Copyright Law. This consent does not extend to copying or transmission by any means—graphic or electronic—for any other purpose, such as for general distribution, for advertising or promotional purposes, for creating a new collective work, for resale, or for information storage and retrieval systems. The copying fee is $0.75 per page. Please report your copying to the Copyright Clearance Center with this code: 1047-8329/91/$00.00+.75. The citation of trade names 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 services referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license 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 patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publication, even without specific indication thereof, are not to be considered unprotected by law. PRINTED IN THE UNITED STATES OF AMERICA

University of California—Berkeley

Julius J. Menn

Malcolm H. Chisholm

Plant Sciences Institute, U.S. Department of Agriculture

Indiana University

Marshall Phillips Natalie Foster Lehigh University

Office of Agricultural Biotechnology, U.S. Department of Agriculture

Dennis W. Hess

Daniel M. Quinn

Lehigh University

University of Iowa

Mary A. Kaiser

A. Truman Schwartz

E. I. du Pont de Nemours and

Macalaster College

Company

Stephen A. Szabo Gretchen S. Kohl

Conoco Inc.

Dow-Corning Corporation

Robert A. Weiss Michael R. Ladisch Purdue University

University of Connecticut

Foreword

Contributors

We thank the following corporations and Herchel Smith for their generous financial support of the series Profiles, Pathways, and Dreams.

In 1986, the ACS Books Department accepted for publication a collec­ tion of autobiographies of organic chemists, to be published in a single volume. However, the authors were much more prolific than the project's editor, Jeffrey I. Seeman, had anticipated, and under his gui­ dance and encouragement, the project took on a life of its own. The original volume evolved into 22 volumes, and the first volume of Pro­ files, Pathways, and Dreams: Autobiographies of Eminent Chemists was published in 1990. Unlike the original volume, the series was structured to include chemical scientists in all specialties, not just organic chemistry. Our hope is that those who know the authors will be confirmed in their admiration for them, and that those who do not know them will find these eminent scientists a source of inspiration and encouragement, not only in any scientific endeavors, but also in life.

Akzo nv

Pfizer Inc.

Bachem Inc.

Philip Morris

E. I. du Pont de Nemours and Company

Quest International

Duphar B.V.

Sandoz Pharmaceuticals Corporation

Eisai Co., Ltd.

Sankyo Company, Ltd.

Fujisawa Pharmaceutical Co., Ltd.

Schering-Plough Corporation

Hoechst Celanese Corporation

Shionogi Research Laboratories, Shionogi & Co., Ltd.

Imperial Chemical Industries PLC M. Joan Comstock Head, Books Department American Chemical Society

Herchel Smith Kao Corporation Mitsui Petrochemical Industries, Ltd.

Suntory Institute for Bioorganic Research

The NutraSweet Company

Takasago International Corporation

Organon International B.V.

Takeda Chemical Industries, Ltd.

Pergamon Press PLC

Unilever Research U.S., Inc.

Profiles, Pathways, a/zd Dreams Titles in This Series Sir Derek H. R. Barton Some Recollections of Gap Jumping Arthur J. Birch To See the Obvious

About the Editor

Melvin Calvin Following the Trail of Light: A Scientific Odyssey Donald J. Cram From Design to Discovery Michael J. S. Dewar A Semiempirical Life Carl Djerassi Steroids Made It Possible Ernest L. Eliel From Cologne to Chapel Hill Egbert Havinga Enjoying Organic Chemistry, 1927-1987 Rolf Huisgen Mechanisms, Novel Reactions, Synthetic Principles William S. Johnson A Fifty-Year Love Affair with Organic Chemistry Raymond U. Lemieux Explorations with Sugars: How Sweet It Was Herman Mark From Small Organic Molecules to Large: A Century y of Progress Bruce Merrifield The Concept and Development of Solid-Phase Peptide Synthesis Teruaki Mukaiyama To Catch the Interesting While Running Koji Nakanishi A Wandering Natural Products Chemist Tetsuo Nozoe Seventy Years in Organic Chemistry Vladimir Prelog My 132 Semesters of Chemistry Studies John D. Roberts The Right Place at the Right Time Paul von Rague Schleyer From the Ivy League into the Honey Pot F. G. A. Stone Organometallic Chemistry Andrew Streitwieser, Jr. A Lifetime of Synergy with Theory and Experiment Cheves Walling Fifty Years of Free Radicals

JEFFREY I. SEEMAN received his B.S. with

high honors in 1967 from the Stevens Institute of Technology in Hoboken, New Jersey, and his Ph.D. in organic chemistry in 1971 from the University of California, Berkeley. Following a two-year staff fel­ lowship at the Laboratory of Chemical Physics of the National Institutes of Health in Bethesda, Maryland, he joined the Philip Morris Research Center in Rich­ mond, Virginia, where he is currently a section leader. In 1983-1984, he enjoyed a sabbatical year at the Dyson Perrins Laboratory in Oxford, England, and claims to have visited more than 90% of the castles in England, Wales, and Scotland. Seeman's 80 published papers include research in the areas of pho­ tochemistry, nicotine and tobacco alkaloid chemistry and synthesis, conformational analysis, pyrolysis chemistry, organotransition metal chemistry, the use of cyclodextrins for chiral recognition, and structure-activity relationships in olfaction. He was a plenary lecturer at the Eighth IUPAC Conference on Physical Organic Chemistry held in Tokyo in 1986 and has been an invited lecturer at numerous scien­ tific meetings and universities. Currently, Seeman serves on the Petroleum Research Fund Advisory Board. He continues to count Nero Wolfe and Archie Goodwin among his best friends.

Contents

List of Photographs

xjjj

xvii

Preface

Editor's Note

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A Wandering Natural Products Chemist

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Hong Kong, Lyon, and Alexandria

3

Preuniversity Schooling in Japan

6

Nagoya Imperial University during the War

9

Nagoya Imperial University after the War, 1945-1950

10

Harvard Period, 1950—1952

21

Second Nagoya Period, 1952-1957

29

Tokyo Period, April 1958-March 1963

38

The Third IUPAC Symposium on the Chemistry of Natural Products (Kyoto, April 1964)

45

Sendai Period, April 1963-July 1969

54

xi

70

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