Synthesis of the C1-C27 portion of the aplyronines

被引:9
作者
Calter, MA [1 ]
Zhou, JG [1 ]
机构
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/j.tetlet.2004.04.159
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C-5-C-14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C-15-G(20) of the targets. Further elaboration and an additional coupling led to an intermediate containing C-1-C-27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4847 / 4850
页数:4
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共 28 条
[11]   ENANTIOSPECIFIC PREPARATION OF THE LACTONE FRAGMENT OF MURISOLIN .8. [J].
HARMANGE, JC ;
FIGADERE, B ;
HOCQUEMILLER, R .
TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :347-350
[12]   Total synthesis of oleandolide [J].
Hu, T ;
Takenaka, N ;
Panek, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9229-9230
[13]   A total synthesis of FK-506 [J].
Ireland, RE ;
Gleason, JL ;
Gegnas, LD ;
Highsmith, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :6856-6872
[14]   TOTAL SYNTHESIS OF APLYRONINE-A, A POTENT ANTITUMOR SUBSTANCE OF MARINE ORIGIN [J].
KIGOSHI, H ;
OJIKA, M ;
ISHIGAKI, T ;
SUENAGA, K ;
MUTOU, T ;
SAKAKURA, A ;
OGAWA, T ;
YAMADA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7443-7444
[15]   AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES [J].
LEVIN, JI ;
TUROS, E ;
WEINREB, SM .
SYNTHETIC COMMUNICATIONS, 1982, 12 (13) :989-993
[16]   Stereoselective synthesis of C5-C20 and C21-C34 subunits of the core structure of the aplyronines. Applications of enantioselective additions of chiral allenylindium reagents to chiral aldehydes [J].
Marshall, JA ;
Johns, BA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1501-1510
[17]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[18]   OXIDATION OF ALCOHOLS BY ACTIVATED DIMETHYL-SULFOXIDE - PREPARATIVE, STERIC AND MECHANISTIC STUDY [J].
OMURA, K ;
SWERN, D .
TETRAHEDRON, 1978, 34 (11) :1651-1660
[19]   SULFUR TRIOXIDE IN OXIDATION OF ALCOHOLS BY DIMETHYL SULFOXIDE [J].
PARIKH, JR ;
DOERING, WVE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5505-&
[20]   Studies in marine macrolide synthesis: stereocontrolled synthesis of a C21-C34 subunit of the aplyronines [J].
Paterson, I ;
Blakey, SB ;
Cowden, CJ .
TETRAHEDRON LETTERS, 2002, 43 (34) :6005-6008