Synthetic studies on reidispongiolide A, an actin-depolymerizing marine macrolide: synthesis of C11-C22 and C23-C35 segments

被引：2

作者：

Akiyama, Satoshi ^{[1
]}

Toriihara, Eisuke ^{[1
]}

Suzuki, Kazushi ^{[1
]}

Teruya, Toshiaki ^{[1
]}

Suenaga, Kiyotake ^{[1
]}

机构：

[1] Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 35期

关键词：

POTENT CYTOTOXIC MACROLIDES; BETA-HYDROXY KETONES; STEREOCONTROLLED SYNTHESIS; STEREOCHEMICAL ASSIGNMENT; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; ALDOL REACTIONS; FRAGMENT; SPHINXOLIDES; REDUCTION;

D O I：

10.1016/j.tetlet.2009.06.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C11-C22 and C23-C35 segments 2 and 3 of reidispongiolide A (1), an actin-depolymerizing marine macrolide, were synthesized enantioselectively in 12 steps from (R)-glycidyl trityl ether and in 12 steps from chiral ketone 15, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5012 / 5014

页数：3

共 35 条

[1] Actin-targeting natural products: structures, properties and mechanisms of action [J].

Allingham, J. S. ;

Klenchin, V. A. ;

Rayment, I. .

CELLULAR AND MOLECULAR LIFE SCIENCES, 2006, 63 (18) :2119-2134

[2] Structures of microfilament destabilizing toxins bound to actin provide insight into toxin design and activity [J].

Allingham, JS ;

Zampella, A ;

D'Auria, MV ;

Rayment, I .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (41) :14527-14532

[3]

Bassarello C, 2001, EUR J ORG CHEM, V2001, P39, DOI 10.1002/1099-0690(200101)2001:1<39::AID-EJOC39>3.0.CO

[4]

2-9

[5] Sphinxolides E-G and reidispongiolide C:: Four new cytotoxic macrolides from the New Caledonian Lithistida sponges N-superstes and R-coerulea [J].

Carbonelli, S ;

Zampella, A ;

Randazzo, A ;

Debitus, C ;

Gomez-Paloma, L .

TETRAHEDRON, 1999, 55 (51) :14665-14674

[6] 3 NEW POTENT CYTOTOXIC MACROLIDES CLOSELY-RELATED TO SPHINXOLIDE FROM THE NEW CALEDONIAN SPONGE NEOSIPHONIA-SUPERSTES [J].

DAURIA, MV ;

PALOMA, LG ;

MINALE, L ;

ZAMPELLA, A ;

VERBIST, JF ;

ROUSSAKIS, C ;

DEBITUS, C .

TETRAHEDRON, 1993, 49 (38) :8657-8664

[7] REIDISPONGIOLIDE-A AND REIDISPONGIOLIDE-B, 2 NEW POTENT CYTOTOXIC MACROLIDES FROM THE NEW-CALEDONIAN SPONGE REIDISPONGIA-COERULEA [J].

DAURIA, MV ;

PALOMA, LG ;

MINALE, L ;

ZAMPELLA, A ;

VERBIST, JF ;

ROUSSAKIS, C ;

DEBITUS, C ;

PATISSOU, J .

TETRAHEDRON, 1994, 50 (16) :4829-4834

[8] A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].

DeMico, A ;

Margarita, R ;

Parlanti, L ;

Vescovi, A ;

Piancatelli, G .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977

[9] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[10] SAMARIUM-CATALYZED INTRAMOLECULAR TISHCHENKO REDUCTION OF BETA-HYDROXY KETONES - A STEREOSELECTIVE APPROACH TO THE SYNTHESIS OF DIFFERENTIATED ANTI 1,3-DIOL MONOESTERS [J].

EVANS, DA ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6447-6449

← 1 2 3 4 →