Total synthesis of putative montamine and a proposed structural reassignment

被引：7

作者：

Blair, Lachlan M. ^{[1
]}

Davie, Elizabeth A. Colby ^{[2
]}

Sperry, Jonathan ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1, New Zealand

[2] Assumption Coll, Worcester, MA 01609 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 35期

关键词：

OXIDATION CHEMISTRY; PRODUCTS;

D O I：

10.1039/c4ob01304b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural product montamine was originally assigned as a homodimer of moschamine linked by a N-N' bond at the serotonin side-chain. A total synthesis of the reported structure has shown this to be incorrect. Analysis of the spectroscopic data suggests that the dimerization site has been incorrectly assigned, and montamine is likely to be a 4,4'-bismoschamine natural product previously described in the literature.

引用

页码：6878 / 6884

页数：7

共 18 条

[1] Selective cleavage of isopropyl aryl ethers by aluminum trichloride [J].

Banwell, MG ;

Flynn, BL ;

Stewart, SG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :9139-9144

[2]

BISHOP GJ, 1967, J CHEM SOC CHEM COMM, P672

[3] Natural Products Containing a Nitrogen-Nitrogen Bond [J].

Blair, Lachlan M. ;

Sperry, Jonathan .

JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :794-812

[4] Studies towards the synthesis of montamine: synthesis of the 1,2-bis(indolyl)ethylhydrazine fragment [J].

Blair, Lachlan M. ;

Sperry, Jonathan .

TETRAHEDRON LETTERS, 2013, 54 (15) :1980-1982

[5] Effective strategy for the systematic synthesis of hydrazine derivatives [J].

Bredihhin, Aleksei ;

Maeorg, Uno .

TETRAHEDRON, 2008, 64 (28) :6788-6793

[6] REACTION OF MALONDIALDEHYDE WITH AMINE NEUROTRANSMITTERS - FORMATION AND OXIDATION CHEMISTRY OF FLUORESCENT 1,4-DIHYDROPYRIDINE ADDUCTS [J].

DISCHIA, M ;

NAPOLITANO, A ;

COSTANTINI, C .

TETRAHEDRON, 1995, 51 (34) :9501-9508

[7] Bidirectional synthesis of montamine analogs [J].

Freitas, Melanie B. ;

Simollardes, Kelly A. ;

Rufo, Caroline M. ;

McLellan, Chantel N. ;

Dugas, Gabrielle J. ;

Lupien, Leslie E. ;

Davie, Elizabeth A. Colby .

TETRAHEDRON LETTERS, 2013, 54 (40) :5489-5491

[8] Z/E Isomerism in Nα-Nα-Disubstituted Hydrazides and the Amidoxy Bond: Application to the Conformational Analysis of Pseudopeptides Built of Hydrazinoacids and α-Aminoxyacids [J].

Le Grel, Philippe ;

Salauen, Arnaud ;

Mocquet, Clemence ;

Le Grel, Barbara ;

Roisnel, Thierry ;

Potel, Michel .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) :8756-8767

[9] Oxidative polymerisation of 5,6-dihydroxyindole-2-carboxylic acid to melanin: A new insight [J].

Pezzella, A ;

Napolitano, A ;

dIschia, M ;

Prota, G .

TETRAHEDRON, 1996, 52 (23) :7913-7920

[10] Moschamine, cis-moschamine, moschamindole and moschamindolol: Four novel indole alkaloids from Centaurea moschata [J].

Sarker, SD ;

Savchenko, T ;

Whiting, P ;

Sik, V ;

Dinan, LN .

NATURAL PRODUCT LETTERS, 1997, 9 (03) :189-199

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