Total synthesis of mycothiazole, a polyketide heterocycle from marine sponges

被引：42
|
作者：
Sugiyama, H
Yokokawa, F
Shioiri, T [1 ]
机构：
[1] Meijo Univ, Grad Sch Environm & Human Sci, Nagoya, Aichi 4688502, Japan
[2] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
来源：
TETRAHEDRON | 2003年 / 59卷 / 34期
关键词：
chemical manganese dioxide; Stille coupling; aldol reaction; marine natural product; absolute configuration;
D O I：
10.1016/S0040-4020(03)01020-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mycothiazole isolated from marine sponges has been efficiently synthesized in a convergent manner. The key reactions involve the thiazole synthesis by dehydrogenation of the thiazolidine with chemical manganese dioxide (CMD), the Stille coupling, and the Nagao asymmetric acetate aldol reaction using the chiral 1,3-thiazolidine-2-thione. This synthesis clearly established the absolute configuration of natural mycothiazole to be (R). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6579 / 6593
页数：15
相关论文
共 50 条
  • [31] Sterols from six marine sponges
    Santalova, EA
    Makarieva, TN
    Gorshkova, IA
    Dmitrenok, AS
    Krasokhin, VB
    Stonik, VA
    BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 2004, 32 (02) : 153 - 167
  • [32] Antifungal metabolites from marine sponges
    Li, HY
    Matsunaga, S
    Fusetani, N
    CURRENT ORGANIC CHEMISTRY, 1998, 2 (06) : 649 - 682
  • [33] Kinase Inhibitors from Marine Sponges
    Skropeta, Danielle
    Pastro, Natalie
    Zivanovic, Ana
    MARINE DRUGS, 2011, 9 (10) : 2131 - 2154
  • [34] Bioactive substances from marine sponges
    Fusetani, N
    JOURNAL OF TOXICOLOGY-TOXIN REVIEWS, 1996, 15 (02): : 157 - 170
  • [35] Spongian diterpenoids from marine sponges
    Keyzers, RA
    Northcote, PT
    Davies-Coleman, MT
    NATURAL PRODUCT REPORTS, 2006, 23 (02) : 321 - 334
  • [36] Novel actinobacteria from marine sponges
    Naomi F. Montalvo
    Naglaa M. Mohamed
    Julie J. Enticknap
    Russell T. Hill
    Antonie van Leeuwenhoek, 2005, 87 : 29 - 36
  • [37] Anticancer agents from marine sponges
    Ye, Jianjun
    Zhou, Feng
    Al-Kareef, Ammar M. Q.
    Wang, Hong
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2015, 17 (01) : 64 - 88
  • [38] Novel actinobacteria from marine sponges
    Montalvo, NF
    Mohamed, NM
    Enticknap, JJ
    Hill, RT
    ANTONIE VAN LEEUWENHOEK INTERNATIONAL JOURNAL OF GENERAL AND MOLECULAR MICROBIOLOGY, 2005, 87 (01): : 29 - 36
  • [39] BIOACTIVE COMPOUNDS FROM MARINE SPONGES
    HIGA, T
    TANAKA, J
    KITAMURA, A
    KOYAMA, T
    TAKAHASHI, M
    UCHIDA, T
    PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) : 2227 - 2230
  • [40] Cytotoxic peptides from marine sponges
    Gulavita, NK
    Wright, AE
    McCarthy, PJ
    Pomponi, SA
    Longley, RE
    JOURNAL OF NATURAL TOXINS, 1996, 5 (02) : 225 - 234
12345