Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules Yuichi Kobayashi Editor

Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules Yuichi Kobayashi Editor Cutting-Edge Organic Synthesis and Chemical Biology of Bioactive Molecules The Shape of Organic Synthesis to Come Editor Yuichi Kobayashi Department of Biotechnology Tokyo Institute of Technology Yokohama, Japan ISBN 978-981-13-6243-9 ISBN 978-981-13-6244-6 (eBook) https://doi.org/10.1007/978-981-13-6244-6 © Springer Nature Singapore Pte Ltd. 2019 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. 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The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721, Singapore Preface The purpose of organic synthesis is to provide target compounds by selective meth- ods with high optical purity. Many transition metal-catalyzed asymmetric reactions and reactions catalyzed by organocatalysts have been developed to efficiently reach the goals. Reducing and oxidizing reagents that are highly chemoselective and/or environmentally friendly are also indispensable tools toward the purpose. On the other hand, analytical techniques have advanced to allow swift determination of the efficiency of reactions and the structures. For example, LC-MS analysis equipped with a chiral column could determine the chirality of the structure. Such new reactions and the advances in analytical techniques produced new power for organic synthesis to foray into fields, which used to be considered out of organic synthesis. As a consequence, many interdisciplinary areas have emerged, attracted attention of chemists, and rapidly grown. This book was planned to grasp the latest and excellent achievements in organic synthesis, which are expected to be grown more in the future. On the other hand, the background of each chapter is explained. I hope that the chapters will be understood easily by researchers, especially young, and stimulate research in the future. Chapters “Microbial Fraction Library: A Screening Source for Drug Discovery”, “Efficient Total Synthesis ofŌ mura Natural Products”, “Enantioselective Total Synthesis of the Antitumor Polycyclic Natural Products FR182877 and Taxol”, “Synthetic Approaches on the Pluramycin-Class Antibiotics”, “Recent Progress Toward the Total Synthesis of Duocarmycins A and SA, Yatakemycin, and PDE-I and –II”, “Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis”, “Substitution of Allylic Picolinates with Various Copper Reagents and Synthetic Applications”, “Total Synthesis of Ingenol” present isolation, elucidation, and organic syntheses of several compounds that are naturally occurring. Organic synthesis and biosynthesis of metabolites of polyunsaturated fatty acids are described in chapters “Strategies for the Synthesis of Anti-inflammatory Metabolites of Unsaturated Fatty Acids” and “Biosynthesis, Biological Functions, and Receptors of Leukotriene B4 and 12(S)-Hydroxyheptadecatrienoic Acid”, respectively. Chapter “Synthesis of Classical/Nonclassical Hybrid Cannabinoids and Related Compounds” deals with natural and unnatural cannabinoids and would be helpful to design new v vi Preface medical cannabinoids. Chapters “Exploring Bioactive Marine Natural Products and Identification of Their Molecular Targets”, “Target Protein Chemical Modification”, “Target Identification of Bioactive Compounds by Photoaffinity Labeling Using Diazido Probes” explain chemical biology focusing on tools that are designed based on organic reaction and/or interaction with target proteins. The project of publishing this book began with an invitation of Mr. S. Koizumi, Springer Japan. I sincerely acknowledge Ms. A. Komada of Springer and Ms. M. Shimoda in our laboratory for checking the chapters carefully. Yokohama, Japan Yuichi Kobayashi Contents 1 Microbial Fraction Library: A Screening Source for Drug Discovery �� 1 Toshihiko Nogawa, Julius Adam V. Lopez, and Hiroyuki Osada 2 Efficient Total Synthesis of Ōmura Natural Products �� 21 Toshiaki Sunazuka, Tomoyasu Hirose, and Satoshi Ōmura 3 Enantioselective Total Synthesis of the Antitumor Polycyclic Natural Products FR182877 and Taxol �� 49 Masahisa Nakada 4 Synthetic Approaches on the Pluramycin-Class Antibiotics �� 75 Yoshio Ando, Kei Kitamura, Takashi Matsumoto, and Keisuke Suzuki 5 Recent Progress on the Total Synthesis of Duocarmycins A and SA, Yatakemycin, and PDE-I and PDE-II �� 101 Juri Sakata and Hidetoshi Tokuyama 6 Structure-Activity Relationship Studies of Maitotoxin Based on Chemical Synthesis �� 125 Tohru Oishi 7 Substitution of Allylic Picolinates with Various Copper Reagents and Synthetic Applications �� 145 Yuichi Kobayashi and Miwa Shimoda 8 Total Synthesis of Ingenol �� 171 Tyler F. Higgins and Jeffrey D. Winkler 9 Strategies for the Synthesis of Anti-inflammatory Metabolites of Unsaturated Fatty Acids �� 193 Yuichi Kobayashi and Masao Morita vii viii Contents 10 Biosynthesis, Biological Functions, and Receptors of Leukotriene B4 and 12(S)-Hydroxyheptadecatrienoic Acid �� 233 Toshiaki Okuno and Takehiko Yokomizo 11 Synthesis of Classical/Nonclassical Hybrid Cannabinoids and Related Compounds �� 247 Thanh C. Ho and Marcus A. Tius 12 Exploring Bioactive Marine Natural Products and Identification of Their Molecular Targets �� 291 Masayoshi Arai 13 Target Protein Chemical Modification �� 305 Hiroyuki Nakamura 14 Target Identification of Bioactive Compounds by Photoaffinity Labeling Using Diazido Probes �� 335 Suguru Yoshida and Takamitsu Hosoya List of Figures Fig. 1.1 Screening strategy of interesting secondary metabolites................. 2 Fig. 1.2 Morphological profiles of HeLa and srcts-NRK cancer cells treated with pyrrolizilactone.................................................... 5 Fig. 1.3 Concept of the fraction library......................................................... 7 Fig. 1.4 Culture condition and preparation of crude extracts and fractions....................................................................... 8 Fig. 1.5 A basic concept of 2D separation for the preparation of fractions....................................................................................... 9 Fig. 1.6 Mass distribution of fractions.......................................................... 9 Fig. 1.7 General activity profile of the fraction library evaluated at 100 μg/mL.................................................................................... 10 Fig. 1.8 NPPlots and unusual alignments...................................................... 11 Fig. 1.9 NPPlots and specific metabolite group of Streptomyces sp. RK88–1355...................................................................................... 11 Fig. 1.10 Structure and putative biosynthetic pathway of verticilactam......... 12 Fig. 1.11 Structures and putative biosynthetic pathway of spirotoamides...... 13 Fig. 1.12 Structures of octaminomycins A and B........................................... 14 Fig. 1.13 NPPlot of Streptomyces sp. RK88–1355 and new antimycin-related metabolites.......................................................... 15 Fig. 1.14 Structural diversity of the antimycin class of metabolites............... 16 Fig. 1.15 Variety of the functional group at C-3 position............................... 17 Fig. 2.1 Our strategy...................................................................................... 22 Fig. 2.2 Structures of novel Ōmura natural products.................................... 23 Fig. 2.3 Structures of pyripyropenes............................................................. 24 Fig. 2.4 Biosynthesis of pyripyropene A......................................................

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