Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment

Francisco Sánchez-Izquierdo; Pilar Blanco; Félix Busqué; Ramón Alibés; Pedro De March; Marta Figueredo; Josep Font; Teodor Parella

doi:10.1021/ol070486p

Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment

Francisco Sánchez-Izquierdo, Pilar Blanco, Félix Busqué, Ramón Alibés, Pedro De March, Marta Figueredo, Josep Font, Teodor Parella

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Abstract

The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine. © 2007 American Chemical Society.

Original language	English
Pages (from-to)	1769-1772
Journal	Organic Letters
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/ol070486p
Publication status	Published - 26 Apr 2007

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title = "Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment",

abstract = "The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine. {\textcopyright} 2007 American Chemical Society.",

author = "Francisco S{\'a}nchez-Izquierdo and Pilar Blanco and F{\'e}lix Busqu{\'e} and Ram{\'o}n Alib{\'e}s and {De March}, Pedro and Marta Figueredo and Josep Font and Teodor Parella",

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T1 - Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment

AU - Sánchez-Izquierdo, Francisco

AU - Blanco, Pilar

AU - Busqué, Félix

AU - Alibés, Ramón

AU - De March, Pedro

AU - Figueredo, Marta

AU - Font, Josep

AU - Parella, Teodor

PY - 2007/4/26

Y1 - 2007/4/26

N2 - The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine. © 2007 American Chemical Society.

AB - The total synthesis of the putative structure of the Stemona alkaloid stemonidine has been completed. The key transformations include a 1,3-dipolar cycloaddition of a chiral nitrone derived from (S)-prolinol and a spirolactonization process involving the generation of the critical stereocenter. The NMR data of the synthetic material do not match those reported for the natural product. It is concluded that the structure assigned to stemonidine is incorrect, and it must be reassigned as stemospironine. © 2007 American Chemical Society.

U2 - 10.1021/ol070486p

DO - 10.1021/ol070486p

M3 - Article

SN - 1523-7060

VL - 9

SP - 1769

EP - 1772

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Total synthesis of the putative structure of stemonidine: The definitive proof of misassignment

Abstract

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