Enantioselective Total Synthesis of Amphidinolide F

被引：40

作者：

Mahapatra, Subham ^{[1
]}

Carter, Rich G. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 32期

基金：

美国国家卫生研究院;

关键词：

asymmetric synthesis; diene; macrolide; silver catalysis; umpolung; ABSOLUTE STEREOCHEMISTRY; CYTOTOXIC MACROLIDE; EFFICIENT SYNTHESIS; C(1)-C(9) FRAGMENT; SULFONES;

D O I：

10.1002/anie.201203935

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A common-intermediate approach is utilized in the total synthesis of amphidinolide F (see scheme, left) to access both the C1-C8 and the C18-C25 portions of the macrolide. A silver-catalyzed rearrangement/cyclization was employed to construct the two tetrahydrofuran rings. A Felkin-controlled, dienyl lithium addition to an α-chiral aldehyde incorporated both the C9-C11 diene and the alcohol at C8. An umpolung sulfone alkylation/oxidative desulfurization sequence is employed to couple the two moieties. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7948 / 7951

页数：4

共 57 条

[1] Synthetic studies on amphidinolides C and F: synthesis of the C18-C29 segment of amphidinolide F [J].

Armstrong, Alan ;

Pyrkotis, Constantina .

TETRAHEDRON LETTERS, 2009, 50 (26) :3325-3328

[2] Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C [J].

Bates, Robert H. ;

Shotwell, J. Brad ;

Roush, William R. .

ORGANIC LETTERS, 2008, 10 (19) :4343-4346

[3] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].

Blakemore, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585

[4] Novel Aerobic Oxidation of Primary Sulfones to Carboxylic Acids [J].

Bonaparte, Amy C. ;

Betush, Matthew P. ;

Panseri, Bettina M. ;

Mastarone, Daniel J. ;

Murphy, Ryan K. ;

Murphree, S. Shaun .

ORGANIC LETTERS, 2011, 13 (06) :1447-1449

[5] Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans [J].

Buzas, A ;

Istrate, F ;

Gagosz, F .

ORGANIC LETTERS, 2006, 8 (09) :1957-1959

[6] Total Syntheses of (+)-Tedanolide and (+)-13-Deoxytedanolide [J].

Dunetz, Joshua R. ;

Julian, Lisa D. ;

Newcom, Jason S. ;

Roush, William R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) :16407-16416

[7] Efficient Synthesis of the C(1)-C(9) Fragment of Amphidinolides C, C2, and F [J].

Ferrie, Laurent ;

Figadere, Bruno .

ORGANIC LETTERS, 2010, 12 (21) :4976-4979

[8]

Fischer D. A., 2012, 243 NAT AM CHEM SOC

[9] A stereoselective and short total synthesis of the polyhydroxylated γ-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes [J].

Flögel, O ;

Amombo, MGO ;

Reissig, HU ;

Zahn, G ;

Brüdgam, I ;

Hartl, H .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1405-1415

[10] Synthetic studies on antascomicin A: construction of the C18-C34 fragment [J].

Fuwa, H ;

Okamura, Y ;

Natsugari, H .

TETRAHEDRON, 2004, 60 (25) :5341-5352

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