Experimental and theoretical study of stereochemistry for new pseurotin A3 with an unusual hetero-spirocyclic system. Issue 45 (10th November 2016)

• Record Type: Journal Article
• Authors: Xu, Lan-Lan; Cao, Fei; Yang, Qin; Li, Wan; Tian, Sha-Sha; Zhu, Hua-Jie; Zhao, Yan-Yan; Yang, Xun
• Is Part Of: Tetrahedron. Volume 72:Issue 45(2016)
• Page Start: 7194
• Page End: 7199
• Publication Date: 2016-11-10
• Subjects: Pseurotin A3 -- Chiroptical spectroscopies -- 13C NMR -- Absolute configuration; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.09.053
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new pseurotin A3 (3 ), which was obtained from the fungus Aspergillus terreus was converted into its acetyl derivative (4 ). Optical rotation (OR), 13 C NMR, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) were measured for (+)-4 and computed for four possible isomers using quantum theory. Absolute configuration of (+)-4 was finally assigned as (5 S, 8 S, 9 R, 10 S, 11 R, 12 Z ) by comparing the predicted OR, ECD and VCD spectra to the experimental data. Therefore, the new compound3 should have the (5 S, 8 S, 9 R, 10 S, 11 R, 12 Z ) too. Graphical abstract: