Total synthesis of 2′-O-methylmyxalamide D and (6E)-2′-O-methylmyxalamide D

被引：57

作者：

Coleman, Robert S. ^{[1
]}

Lu, Xiaoling ^{[1
]}

Modolo, Isabelle ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 13期

关键词：

D O I：

10.1021/ja070265e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hetero-bis-metalated 1,3,5-hexatrienes are employed in the linchpin coupling of synthetic fragments for the convergent construction of the central pentaene of the antifungal agent 2'-O-methylmyxalamide D and its (6E) isomer. Sequential Stille and Suzuki-Miyaura couplings interpolate the boron/tin triene into the pentaene chain. The total synthesis of O-methylmyxalamide D and its (6E) isomer was accomplished efficiently.

引用

页码：3826 / +

页数：3

共 29 条

[11] Biosynthesis of 2′-O-methylmyxalamide D in the myxobacterium Cystobacter fuscus:: a polyketide synthase-nonribosomal peptide synthetase system for the myxalamide D skeleton and a methyltransferase for the final O-methylation [J].

Feng, ZY ;

Qi, JH ;

Tsuge, T ;

Oba, Y ;

Sakagami, Y ;

Ojika, M .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2006, 70 (03) :699-705

[12] ANTIBIOTICS FROM GLIDING BACTERIA .14. THE MYXALAMIDS, NEW ANTIBIOTICS FROM MYXOCOCCUS-XANTHUS (MYXOBACTERALES) .1. PRODUCTION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES, AND MECHANISM OF ACTION [J].

GERTH, K ;

JANSEN, R ;

REIFENSTAHL, G ;

HOFLE, G ;

IRSCHIK, H ;

KUNZE, B ;

REICHENBACH, H ;

THIERBACH, G .

JOURNAL OF ANTIBIOTICS, 1983, 36 (09) :1150-1156

[13] CONVENIENT GENERATION OF 1-PROPYNYLLITHIUM - ONE-POT SYNTHESIS OF ACETYLENIC CARBINOLS FROM 1,2-DIBROMOPROPANE AND ALDEHYDES AND KETONES [J].

GRIBBLE, GW ;

JOYNER, HH ;

SWITZER, FL .

SYNTHETIC COMMUNICATIONS, 1992, 22 (20) :2997-3002

[14] Oxidation of olefins by palladium(II) .15. Oxidation of (R)-(-)-(Z)- and (R)-(+)-(E)-3-penten-2-ol using several nucleophiles to give chiral beta-substituted ketones. A method of finding modes of palladation of olefins using chirality transfer [J].

Hamed, O ;

Henry, PM .

ORGANOMETALLICS, 1997, 16 (22) :4903-4909

[15] Total synthesis of phenalamide A2 [J].

Hoffmann, RW ;

Rohde, T ;

Haeberlin, E ;

Schäfer, F .

ORGANIC LETTERS, 1999, 1 (11) :1713-1715

[16] A convenient and genuine equivalent to HZrCp2Cl generated in situ from ZrCp2Cl2-DIBAL-H [J].

Huang, Zhihong ;

Negishi, Ei-ichi .

ORGANIC LETTERS, 2006, 8 (17) :3675-3678

[17]

JANSEN R, 1983, LIEBIGS ANN CHEM, P1081

[18] Novel antifungal polyene amides from the myxobacterium Cystobacter fuscus:: isolation, antifungal activity and absolute structure determination [J].

Kundim, BA ;

Itou, Y ;

Sakagami, Y ;

Fudou, R ;

Yamanaka, S ;

Ojika, M .

TETRAHEDRON, 2004, 60 (45) :10217-10221

[19] Total synthesis of myxalamide A [J].

Mapp, AK ;

Heathcock, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :23-27

[20] Synthesis and reactions of allylic, allenic, vinylic, and arylmetal reagents from halides and esters via transient organopalladium intermediates [J].

Marshall, JA .

CHEMICAL REVIEWS, 2000, 100 (08) :3163-3185

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