Total Synthesis of Sporolide B

被引:63
作者
Nicolaou, K. C. [1 ]
Tang, Yefeng
Wang, Jianhua
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
cycloaddition; Diels-Alder reactions; natural products; o-quinones; total synthesis; CYCLOADDITION; CHEMISTRY; ENEDIYNE; BIOLOGY; BENZYNE;
D O I
10.1002/anie.200900264
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An ocean of discovery: The first total synthesis of the highly oxygenated, marine-derived, natural product sporolide B has been achieved through a convergent strategy. The key steps involve a rutheniumcatalyzed [2+2+2] cycloaddition to assemble the indene structural motif and a thermally induced Diels-Alder-type reaction to forge the macrocycle (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3449 / 3453
页数:5
相关论文
共 21 条
[1]   Sporolides A and B:: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica [J].
Buchanan, GO ;
Williams, PG ;
Feling, RH ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ORGANIC LETTERS, 2005, 7 (13) :2731-2734
[2]   The preparation of optically active 2-cyclopenten-1,4-diol derivatives from furfuryl alcohol [J].
Curran, TT ;
Hay, DA ;
Koegel, CP ;
Evans, JC .
TETRAHEDRON, 1997, 53 (06) :1983-2004
[3]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[4]   Developing a new resource for drug discovery: marine actinomycete bacteria [J].
Fenical, William ;
Jensen, Paul R. .
NATURE CHEMICAL BIOLOGY, 2006, 2 (12) :666-673
[5]   A 2-STEP, 3-COMPONENT SYNTHESIS OF PGE(1) - UTILIZATION OF ALPHA-IODOENONES IN PD(0)-CATALYZED CROSS-COUPLINGS OF ORGANOBORANES [J].
JOHNSON, CR ;
BRAUN, MP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11014-11015
[6]   PARA BENZYNE - GENERATION AS AN INTERMEDIATE IN A THERMAL ISOMERIZATION REACTION AND TRAPPING EVIDENCE FOR 1,4-BENZENEDIYL STRUCTURE [J].
JONES, RR ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (02) :660-&
[8]   Unraveling the biosynthesis of the sporolide cyclohexenone building block [J].
McGlinchey, Ryan P. ;
Nett, Markus ;
Moore, Bradley S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2406-2407
[9]   Synthesis of the sporolide ring framework through a cascade sequence involving an intramolecular [4+2] cycloaddition reaction of an o-quinone [J].
Nicolaou, K. C. ;
Wang, Jianhua ;
Tang, Yefeng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1432-1435
[10]  
Nicolaou K.C., 1991, Angew. Chem, V103, P1453, DOI DOI 10.1002/CCTC.201501367