Total synthesis of apratoxin A

被引:76
作者
Doi, T [1 ]
Numajiri, Y [1 ]
Munakata, A [1 ]
Takahashi, T [1 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan
关键词
D O I
10.1021/ol052907d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh3(0)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and deprotection of the allyl ester and the Fmoc, followed by macrolactamization provided apratoxin A (1).
引用
收藏
页码:531 / 534
页数:4
相关论文
共 24 条
[1]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[2]   Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A [J].
Chen, JH ;
Forsyth, CJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12067-12072
[3]   Total synthesis of apratoxin A [J].
Chen, JH ;
Forsyth, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) :8734-8735
[4]  
CIOMMER M, 1991, SYNLETT, P593
[5]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[6]   Convergent synthesis of (-)-mirabazole B using a chloroimidazolidium coupling reagent, CIP [J].
Kuriyama, N ;
Akaji, K ;
Kiso, Y .
TETRAHEDRON, 1997, 53 (25) :8323-8334
[7]   Proline-catalyzed direct asymmetric aldol reactions [J].
List, B ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396
[8]   Asymmetric aminocatalysis [J].
List, B .
SYNLETT, 2001, (11) :1675-1686
[9]   Proline-catalyzed asymmetric aldol reactions between ketones and α-unsubstituted aldehydes [J].
List, B ;
Pojarliev, P ;
Castello, C .
ORGANIC LETTERS, 2001, 3 (04) :573-575
[10]   New apratoxins of marine cyanobacterial origin from Guam and Palau [J].
Luesch, H ;
Yoshida, WY ;
Moore, RE ;
Paul, VJ .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) :1973-1978