Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: Synthesis of the tetracyclic core of nakadomarin A

被引：125

作者：

Young, IS ^{[1
]}

Williams, JL ^{[1
]}

Kerr, MA ^{[1
]}

机构：

[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 05期

关键词：

D O I：

10.1021/ol0501018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the tetracyclic core of nakadomarin A is described. The core contains all the heterocycles and the required stereocenters found in the natural product and provides a promising route to the target itself. The strategy utilizes a general, diastereoselective pyrrolidine synthesis that proceeds via a homo 3+2 dipolar cycloaddition. The scope of this methodology is also described.

引用

页码：953 / 955

页数：3

共 24 条

[1] First total synthesis of the marine alkaloids (±)-fasicularin and (±)-lepadiformine based on stereocontrolled intramolecular acylnitroso-Diels-Alder reaction
Abe, H
Aoyagi, S
Kibayashi, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) : 4583 - 4592
[2] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS
ABELMAN, MM
OH, T
OVERMAN, LE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) : 4130 - 4133
[3] A concise asymmetric synthesis of the ADE fragment of nakadomarin
Ahrendt, KA
Williams, RM
[J]. ORGANIC LETTERS, 2004, 6 (24) : 4539 - 4541
[4] Cleavage of N-O bonds promoted by samarium diiodide: Reduction of free or N-acylated O-alkylhydroxylamines
Chiara, JL
Destabel, C
Gallego, P
MarcoContelles, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 359 - 360
[5] SYNTHETIC ROUTES TO CRISTATIC ACID AND DERIVATIVES
CHIARELLO, J
JOULLIE, MM
[J]. TETRAHEDRON, 1988, 44 (01) : 41 - 48
[6] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL
CICCHI, S
GOTI, A
BRANDI, A
GUARNA, A
DESARLO, F
[J]. TETRAHEDRON LETTERS, 1990, 31 (23) : 3351 - 3354
[7] Fürstner A, 2001, CHEM-EUR J, V7, P4811, DOI 10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO
[8] 2-P
[9] Ring closing alkyne metathesis.: Comparative investigation of two different catalyst systems and application to the stereoselective synthesis of olfactory lactones, azamacrolides, and the macrocyclic perimeter of the marine alkaloid nakadomarin A
Fürstner, A
Guth, O
Rumbo, A
Seidel, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) : 11108 - 11113
[10] REDUCTIVE CLEAVAGE OF N-O BONDS IN HYDROXYLAMINE AND HYDROXAMIC ACID-DERIVATIVES USING SMI2/THF
KECK, GE
MCHARDY, SF
WAGER, TT
[J]. TETRAHEDRON LETTERS, 1995, 36 (41) : 7419 - 7422

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