Total Synthesis of 8-Deshydroxyajudazol B

被引：24

作者：

Birkett, Stephen ^{[1
]}

Ganame, Danny ^{[1
]}

Hawkins, Bill C. ^{[1
]}

Meiries, Sebastien ^{[1
]}

Quach, Tim ^{[1
]}

Rizzacasa, Mark A. ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Inst Bio21, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 08期

基金：

澳大利亚研究理事会;

关键词：

AJUDAZOL-A; CHONDROMYCES-CROCATUS; TRANSESTERIFICATION; HYDROBORATION; MYXOBACTERIA; CONVENIENT; ENANTIOMER; EFFICIENT; CATALYST; SYSTEM;

D O I：

10.1021/ol200331u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.

引用

页码：1964 / 1967

页数：4

共 34 条

[11] Total synthesis of aigialomycin D [J].

Geng, XD ;

Danishefsky, SJ .

ORGANIC LETTERS, 2004, 6 (03) :413-416

[12] Stereoselective synthesis of dihydroisocoumarin moiety of microbial agent AI-77-B: a Diels-Alder based strategy [J].

Ghosh, AK ;

Cappiello, J .

TETRAHEDRON LETTERS, 1998, 39 (48) :8803-8806

[13] Formal synthesis of (-)-apicularen A [J].

Graetz, BR ;

Rychnovsky, SD .

ORGANIC LETTERS, 2003, 5 (18) :3357-3360

[14] Oxidative rearrangements of isobenzofurans: Studies toward the synthesis of the ajudazols [J].

Hobson, Stephen J. ;

Parkin, Andrew ;

Marquez, Rodolfo .

ORGANIC LETTERS, 2008, 10 (13) :2813-2816

[15]

Jansen R, 2002, EUR J ORG CHEM, V2002, P917

[16] Enantioselective total synthesis of a potent antitumor antibiotic, fredericamycin A [J].

Kita, Y ;

Higuchi, K ;

Yoshida, Y ;

Iio, K ;

Kitagaki, S ;

Ueda, K ;

Akai, S ;

Fujioka, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3214-3222

[17] Synthesis of the eastern portion of ajudazol A based on stille coupling and double acetylene carbocupration [J].

Krebs, O ;

Taylor, RJK .

ORGANIC LETTERS, 2005, 7 (06) :1063-1066

[18] Ajudazols, new inhibitors of the mitochondrial electron transport from Chondromyces crocatus -: Production, antimicrobial activity and mechanism of action [J].

Kunze, B ;

Rolf, JA ;

Höfle, G ;

Reichenbach, H .

JOURNAL OF ANTIBIOTICS, 2004, 57 (02) :151-155

[19] A CONVENIENT PROCEDURE FOR THE PREPARATION OF 3-BROMOPROPIOLIC ESTERS [J].

LEROY, J .

SYNTHETIC COMMUNICATIONS, 1992, 22 (04) :567-572

[20] Synthesis of the C1-C16 fragment of spirastrellolide A [J].

Liu, Jia ;

Yang, Jin Haek ;

Ko, Changhong ;

Hsung, Richard P. .

TETRAHEDRON LETTERS, 2006, 47 (34) :6121-6123

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