Stereoselective synthesis of the phytotoxic nonenolide herbarumin-I from L-ascorbic acid

被引：32

作者：

Nagaiah, K. ^{[1
]}

Sreenu, D. ^{[1
]}

Rao, R. Srinivasa ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 40期

关键词：

L-ascorbic acid; allylation; vinylation; macrolactonisation; ring-closing metathesis;

D O I：

10.1016/j.tetlet.2007.07.191

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of herbarumin-I in 22% overall yield, starting from L-ascorbic acid derived (S)-2,3-O-isopropylidine glyceraldehyde as a chiral template is reported. Stereoselective allylation and vinylation to control the required stereogenic centres and macrolactonisation followed by a ring-closing metathesis (RCM) are the key steps. (C) 2007 Published by Elsevier Ltd.

引用

页码：7173 / 7176

页数：4

共 31 条

[1] THE CHEMISTRY OF L-ASCORBIC AND D-ISOASCORBIC ACIDS .1. THE PREPARATION OF CHIRAL BUTANETRIOLS AND BUTANETETROLS [J].

ABUSHANAB, E ;

VEMISHETTI, P ;

LEIBY, RW ;

SINGH, HK ;

MIKKILINENI, AB ;

WU, DCJ ;

SAIBABA, R ;

PANZICA, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2598-2602

[2] SECONDARY MOLD METABOLITES .41. STRUCTURE AND BIOSYNTHESIS OF CERCOSPORA-BETICOLA TOXIN (CBT) [J].

ARNONE, A ;

NASINI, G ;

MERLINI, L ;

RAGG, E ;

ASSANTE, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01) :145-151

[3]

CATHY E, 1987, J ORGANOMET CHEM, V322, P177

[4]

CHRISTIAN P, 1985, J ORG CHEM, V50, P910

[5] The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II [J].

Díez, E ;

Dixon, DJ ;

Ley, SV ;

Polara, A ;

Rodríguez, F .

HELVETICA CHIMICA ACTA, 2003, 86 (11) :3717-3729

[6] Decanolides, 10-membered lactones of natural origin [J].

Drager, G ;

Kirschning, A ;

Thiericke, R ;

Zerlin, M .

NATURAL PRODUCT REPORTS, 1996, 13 (05) :365-375

[7] PINOLIDOXIN, A PHYTOTOXIC NONENOLIDE FROM ASCOCHYTA-PINODES [J].

EVIDENTE, A ;

LANZETTA, R ;

CAPASSO, R ;

VURRO, M ;

BOTTALICO, A .

PHYTOCHEMISTRY, 1993, 34 (04) :999-1003

[8] 3 NEW TOXIC PINOLIDOXINS FROM ASCOCHYTA-PINODES [J].

EVIDENTE, A ;

CAPASSO, R ;

ABOUZEID, MA ;

LANZETTA, R ;

VURRO, M ;

BOTTALICO, A .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (11) :1937-1943

[9]

FORTANET JG, 2005, J ORG CHEM, V70, P9822

[10] Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle [J].

Fürstner, A ;

Radkowski, K ;

Wirtz, C ;

Goddard, R ;

Lehmann, CW ;

Mynott, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) :7061-7069

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