Biomimetic synthesis of (-)-longithorone A

被引:177
作者
Layton, ME [1 ]
Morales, CA [1 ]
Shair, MD [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ja016585u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantioseletive, biomimetic synthesis of (-)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene-yne metathesis macrocyclizations. Copyright © 2002 American Chemical Society.
引用
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页码:773 / 775
页数:3
相关论文
共 26 条
[1]   Lovastatin nonaketide synthase catalyzes an intramolecular Diels-Alder reaction of a substrate analogue [J].
Auclair, K ;
Sutherland, A ;
Kennedy, J ;
Witter, DJ ;
Van den Heever, JP ;
Hutchinson, CR ;
Vederas, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) :11519-11520
[2]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[3]  
Eliel E.L., 1994, Stereochemistry of Organic Compounds
[4]  
Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2704, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO
[5]  
2-1
[6]   Longithorones, unique prenylated para- and metacyclophane type quinones from the tunicate Aplidium longithorax [J].
Fu, X ;
Hossain, MB ;
Schmitz, FJ ;
vanderHelm, D .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3810-3819
[7]   LONGITHORONE-A - UNPRECEDENTED DIMERIC PRENYLATED QUINONE FROM THE TUNICATE APLYDIUM-LONGITHORAX [J].
FU, X ;
HOSSAIN, MB ;
VANDERHELM, D ;
SCHMITZ, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12125-12126
[8]  
Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
[9]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[10]   ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS [J].
HOFFMANN, RW .
CHEMICAL REVIEWS, 1989, 89 (08) :1841-1860