Absolute Configuration Assignment of 3′,4′-di-O-acylkhellactones Using Vibrational Circular Dichroism Exciton Chirality

被引：0

作者：

Buendia-Trujillo, Abigail I. ^{[1
]}

Martin Torrres-Valencia, J. ^{[2
]}

Joseph-Nathan, Pedro ^{[3
]}

Burgueno-Tapia, Eleuterio ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Prolongac Carpio & Plan Ayala, Mexico City 11340, DF, Mexico

[2] Univ Autonoma Estado Hidalgo, Area Acad Quim, Mineral Reforma, Hidalgo 42184, Mexico

[3] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

NATURAL PRODUCT COMMUNICATIONS | 2015年 / 10卷 / 06期

关键词：

Prionosciadium thapsoides; Khellactone derivatives; Vibrational circular dichroism exciton chirality; Absolute configuration; X-Ray diffraction; PEUCEDANUM-PRAERUPTORUM DUNN; CONSTITUENTS; COUMARINS; ROOTS; DIHYDROPYRANOCOUMARINS;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The 3'R,4'R absolute configuration (AC) of the angular-type pyranocoumarins (-)-3',4'-di-O-acetylkhellactone (2), (-)-4'-O-acetyl-3'-O-angeloylkhellactone (3), (+)-3'-O-acetyl-4'-O-isobutyroylkhellactone (4), and (-)-3'O-angeloyl-4'-O-senecioylkhellactone (5), isolated from the aerial parts of Prionosciadium thapsoides, was assigned by vibrational circular dichroism exciton chirality (VCDEC), and confirmed by comparison of their VCD frequencies with those calculated using DFT at the B3LYP/DGDZVP level. This again reveals that AC assignments based on optical rotation data are not very confident. Evaluation of Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis of 3, independently confirmed this AC.

引用

页码：1027 / 1032

页数：6

共 34 条

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