Quantum Mechanical-NMR-Aided Configuration and Conformation of Two Unreported Macrocycles Isolated from the Soft Coral Lobophytum sp.: Energy Calculations versus Coupling Constants

Song-Wei Li; Cristina Cuadrado; Li-Gong Yao; Antonio Hernandez Daranas; Yue-Wei Guo

doi:10.1021/acs.orglett.0c01155

Quantum Mechanical-NMR-Aided Configuration and Conformation of Two Unreported Macrocycles Isolated from the Soft Coral Lobophytum sp.: Energy Calculations versus Coupling Constants

Org Lett. 2020 Jun 5;22(11):4093-4096. doi: 10.1021/acs.orglett.0c01155. Epub 2020 May 12.

Authors

Song-Wei Li^{1

2}, Cristina Cuadrado³, Li-Gong Yao¹, Antonio Hernandez Daranas³, Yue-Wei Guo¹

Affiliations

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
² Nanjing University of Chinese Medicine, 138 Xianlin Road, Nanjing 210023, China.
³ Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), La Laguna, 38206 Tenerife, Spain.

PMID: 32396368
DOI: 10.1021/acs.orglett.0c01155

Abstract

Two new macrocyclic cembranoids were isolated from the South China Sea soft coral Lobophytum sp. Quantum mechanical-nuclear magnetic resonance (QM-NMR) methods were decisive in their structural elucidation. Better performance in arriving at definitive structures was obtained by QM-NMR methods upon incorporation of ³J_HH values. The validity of this approach also supported an alternative conformational proposal versus that obtained by X-ray crystallography.

Publication types

Research Support, Non-U.S. Gov't