Aryne Acyl-Alkylation in the General and Convergent Synthesis of Benzannulated Macrolactone Natural Products: An Enantioselective Synthesis of (-)-Curvularin

被引：69

作者：

Tadross, Pamela M. ^{[1
]}

Virgil, Scott C. ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

关键词：

RING-CLOSING-METATHESIS; FORMAL SYNTHESIS; CURVULARIN; (&/-)-DIPLODIALIDE-A; (+)-DIPLODIALIDE-A; METABOLITES; OLEFINS; ESTERS;

D O I：

10.1021/ol100335y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach for the synthesis of benzannulated macrolactone natural products utilizing an aryne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (-)-curvularin, curvulin, and (-)-diplodialide C are reported. Furthermore, the aryne insertion technology has enabled the rapid conversion of simple diplodialide natural products to curvularin, thereby connecting these two biosynthetically distinct classes of compounds via synthetic methods.

引用

页码：1612 / 1614

页数：3

共 28 条

[1] A ring-closing metathesis approach toward formal total synthesis of (+)-diplodialide A [J].

Anand, RV ;

Baktharaman, S ;

Singh, VK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3356-3359

[2] Syntheses of epi-aigialomycin D and deoxy-aigialomycin C via a diastereoselective ring closing metathesis macrocyclization protocol [J].

Bajwa, Naval ;

Jennings, Michael P. .

TETRAHEDRON LETTERS, 2008, 49 (02) :390-393

[3] STUDIES IN RELATION TO BIOSYNTHESIS .20. THE STRUCTURE AND BIOSYNTHESIS OF CURVULARIN [J].

BIRCH, AJ ;

MUSGRAVE, OC ;

RICKARDS, RW ;

SMITH, H .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (NOV) :3146-3152

[4] Total synthesis of secocurvularin, curvulin, and the corresponding carboxylic acids. A convenient application of the enzymatic hydrolysis of acid and base sensitive esters [J].

Bracher, F ;

Krauss, J .

NATURAL PRODUCT LETTERS, 1998, 12 (01) :31-34

[5] A CHEMOENZYMATIC SYNTHESIS OF THE MACROCYCLIC LACTONE (S)-CURVULARIN [J].

BRACHER, F ;

SCHULTE, B .

NATURAL PRODUCT LETTERS, 1995, 7 (01) :65-68

[6]

Bracher F, 1997, LIEBIGS ANN-RECL, P1979

[7] CONSTITUENTS OF SOME CURVULARIA SPECIES [J].

COOMBE, RG ;

JACOBS, JJ ;

WATSON, TR .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (03) :783-&

[8] THE DIRECT ACYL-ALKYLATION OF ARYNES. PREPARATION OF METHYL 2-(2-ACETYLPHENYL)ACETATE [J].

Ebner, David C. ;

Tambar, Uttam K. ;

Stoltz, Brian M. .

ORGANIC SYNTHESES, 2009, 86 :161-+

[9] Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua [J].

Edrada, RA ;

Heubes, M ;

Brauers, G ;

Wray, V ;

Berg, A ;

Gräfe, U ;

Wohlfarth, M ;

Mühlbacher, J ;

Schaumann, K ;

Sudarsono ;

Bringmann, G ;

Proksch, P .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11) :1598-1604

[10] 2-(TRIMETHYLSILYL)ETHYL ESTERS AS CARBOXYL PROTECTING GROUP - APPLICATION IN SYNTHESIS OF (-)-(S)-CURVULARIN [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1977, 60 (08) :3039-3044

← 1 2 3 →