The Absolute Configuration for Inthomycin C: Revision of Previously Published Work with a Reinstatement of the (3R)-Configuration for (-)-Inthomycin C

被引：18

作者：

Hae, Karl J. ^{[1
,2
]}

Hatakeyama, Susumi ^{[3
]}

Urabe, Fumiya ^{[3
]}

Ishihara, Jun ^{[3
]}

Manaviazar, Soraya ^{[1
,2
]}

Grabski, Milosz ^{[1
,2
]}

Maczka, Maciej ^{[1
,2
]}

机构：

[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

[2] Queens Univ Belfast, Ctr Canc Res & Cell Biol CCRCB, Belfast BT9 5AG, Antrim, North Ireland

[3] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 13期

关键词：

STREPTOMYCES-SP; PHTHOXAZOLIN;

D O I：

10.1021/ol501484t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereochemical evidence is presented to demonstrate that (-)-inthomycin C has (3R)- and not (3S)-stereo-chemistry. Careful reappraisal of the previously published work(2-5) now indicates that the Hatakeyama, Hale, Ryu, and Taylor teams all have synthesized (-)-(3R)-inthomycin C. The newly measured [alpha](D) of pure (-)-(3R)-inthomycin C (98% ee) is -7.9 (c 0.33, CHCl3) and not -41.5 (c 0.1, CHCl3) as was previously reported in 2012.

引用

页码：3536 / 3539

页数：4

共 9 条

[1] Amylose conformational transitions in binary DMSO/water mixtures [J].

Cheetham, NWH ;

Tao, LP .

CARBOHYDRATE POLYMERS, 1998, 35 (3-4) :287-295

[2] Asymmetric Total Synthesis of (+)-Inthomycin C via O-Directed Free Radical Alkyne Hydrostannation with Ph3SnH and Catalytic Et3B: Reinstatement of the Zeeck-Taylor (3R)-Structure for (+)-Inthomycin C [J].

Hale, Karl J. ;

Grabski, Milosz ;

Manaviazar, Soraya ;

Maczka, Maciej .

ORGANIC LETTERS, 2014, 16 (04) :1164-1167

[3] A convergent stereoselective total synthesis of racemic phthoxazolin A [J].

Hénaff, N ;

Whiting, A .

ORGANIC LETTERS, 1999, 1 (07) :1137-1139

[4]

HENKEL T, 1991, LIEBIGS ANN CHEM, P367

[5] PHTHOXAZOLIN, A SPECIFIC INHIBITOR OF CELLULOSE BIOSYNTHESIS, PRODUCED BY A STRAIN OF STREPTOMYCES SP [J].

OMURA, S ;

TANAKA, Y ;

KANAYA, I ;

SHINOSE, M ;

TAKAHASHI, Y .

JOURNAL OF ANTIBIOTICS, 1990, 43 (08) :1034-1036

[6] Highly Enantioselective Mukaiyama Aldol Reactions Catalyzed by a Chiral Oxazaborolidinium Ion: Total Synthesis of (-)-Inthomycin C [J].

Senapati, Bidyut Kumar ;

Gao, Lizhu ;

Lee, Sung Il ;

Hwang, Geum-Sook ;

Ryu, Do Hyun .

ORGANIC LETTERS, 2010, 12 (22) :5088-5091

[7] Stereoselective Synthesis of Dienyl-Carboxylate Building Blocks: Formal Synthesis of Inthomycin C [J].

Souris, Caroline ;

Frebault, Frederic ;

Patel, Ashay ;

Audisio, Davide ;

Houk, K. N. ;

Maulide, Nuno .

ORGANIC LETTERS, 2013, 15 (13) :3242-3245

[8] The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach [J].

Webb, Michael R. ;

Addie, Matthew S. ;

Crawforth, Catherine M. ;

Dale, James W. ;

Franci, Xavier ;

Pizzonero, Mathieu ;

Donald, Craig ;

Taylor, Richard J. K. .

TETRAHEDRON, 2008, 64 (21) :4778-4791

[9] Organocatalytic asymmetric syntheses of inthomycins A, B and C [J].

Yoshino, Madoka ;

Eto, Kohei ;

Takahashi, Keisuke ;

Ishihara, Jun ;

Hatakeyama, Susumi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (40) :8164-8174

← 1 →