TANDEM BECKMANN AND HUISGEN-WHITE REARRANGEMENT OF THE 9-AZABICYCLO[3.3.1]NONAN-3-ONE SYSTEM .2. THE 2ND MODE OF THE REARRANGEMENT LEADING TO 6-(PROP-L-ENYL)PIPERIDIN-2-YLACETIC ACID, A VERSATILE INTERMEDIATE FOR THE SYNTHESES OF PIPERIDINE ALKALOIDS (-PINIDINE AND (+)-MONOMORINE-I())

Authors
MURAOKA O ZHENG BZ OKUMURA K TABATA E TANABE G KUBO M
Citation
O. Muraoka et al., TANDEM BECKMANN AND HUISGEN-WHITE REARRANGEMENT OF THE 9-AZABICYCLO[3.3.1]NONAN-3-ONE SYSTEM .2. THE 2ND MODE OF THE REARRANGEMENT LEADING TO 6-(PROP-L-ENYL)PIPERIDIN-2-YLACETIC ACID, A VERSATILE INTERMEDIATE FOR THE SYNTHESES OF PIPERIDINE ALKALOIDS (-PINIDINE AND (+)-MONOMORINE-I()), Journal of the Chemical Society. Perkin transactions. I, (2), 1997, pp. 113-119
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
2
Year of publication
1997
Pages
113 - 119
Database
ISI
SICI code
0300-922X(1997):2<113:TBAHRO>2.0.ZU;2-W
Abstract
The second mode of the Huisgen-White rearrangement of the bicyclic lac tam, (-)-2-ethyl-4-oxo-3,10-diazabicyclo[4.3.1]decane (-)-13, leading to cis-[6-(prop-1-enyl)piperidin-2-yl]acetic acid (-)-9a under alkalin e conditions is described. A reasonable reaction mechanism accounting for the preferable formation of the (E)-propenyl isomer (E)-9a is pres ented. Conversions of the olefinic acid 9a into two piperidine alkaloi ds (+)-pinidine (+)-10 and (-)-dihydropinidine (-)-21, and (-)-cis-2-f ormyl-6-methylpiperidine (-)-22, a key synthetic intermediate for an a nts' trail pheromone (+)-monomorine I (+)-11, are also described.