Total synthesis of (-)-ulapualide A: The danger of overdependence on NMR spectroscopy in assignment of stereochemistry

被引：40

作者：

Pattenden, Gerald ^{[1
]}

Ashweek, Neil J. ^{[1
]}

Baker-Glenn, Charles A. G. ^{[1
]}

Walker, Gary M. ^{[1
]}

Yee, James G. K. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 23期

关键词：

macrocycles; natural products; oxazoles; structure elucidation; total synthesis;

D O I：

10.1002/anie.200700459

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lessons learnt: The asymmetric total synthesis of the macrolide (-)-ulapualide A has been accomplished. Interestingly, the 1H NMR spectrum and chiroptical data of the macrolide and of a previously synthesized diastereoisomer with opposite stereocenters at C3, C28, C29, C30, and C32 were superimposable, which highlights the care that must be taken in the assignment of configurations to complex structures based on NMR spectroscopy. (Chemical Equation Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4359 / 4363

页数：5

共 41 条

[1] Absolute stereochemistry of ulapualide A [J].

Allingham, JS ;

Tanaka, J ;

Marriott, G ;

Rayment, I .

ORGANIC LETTERS, 2004, 6 (04) :597-599

[2] AN EFFICIENT AND STEREOSELECTIVE WITTIG-HORNER SYNTHESIS OF ACYCLIC ALPHA-ENONES WITH BARIUM HYDROXIDE AS SOLID CATALYST [J].

ALVAREZIBARRA, C ;

ARIAS, S ;

BANON, G ;

FERNANDEZ, MJ ;

RODRIGUEZ, M ;

SINISTERRA, V .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) :1509-1511

[3]

Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707

[4] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].

CARPINO, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398

[5] Total synthesis of ulapualide A, a novel tris-oxazole containing macrolide from the marine nudibranch Hexabranchus sanguineus [J].

Chattopadhyay, SK ;

Pattenden, G .

TETRAHEDRON LETTERS, 1998, 39 (33) :6095-6098

[6] A total synthesis of the unique tris-oxazole macrolide ulapualide A produced by the marine nudibranch Hexabranchus sanguineus [J].

Chattopadhyay, SK ;

Pattenden, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2429-2454

[7] Towards a total synthesis of ulapualide A.: Concise synthetic routes to the tris-oxazole ring system and tris-oxazole macrolide core in ulapualides, kabiramides, halichondramides, mycalolides and halishigamides [J].

Chattopadhyay, SK ;

Kempson, J ;

McNeil, A ;

Pattenden, G ;

Reader, M ;

Rippon, DE ;

Waite, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2415-2428

[8]

Endoh N, 2003, HETEROCYCLES, V60, P1567

[9] NICKEL PEROXIDE DEHYDROGENATION OF OXYGEN-CONTAINING, SULFUR-CONTAINING, AND NITROGEN-CONTAINING HETEROCYCLES [J].

EVANS, DL ;

MINSTER, DK ;

JORDIS, U ;

HECHT, SM ;

MAZZU, AL ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (04) :497-501

[10] Synthesis of oxazoles and thiazoles II. [J].

Gabriel, S .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1910, 43 :1283-1287

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