10.1021/acs.joc.8b02912.s003 Qihao Wu Qihao Wu Fei Ye Fei Ye Xiao-Lu Li Xiao-Lu Li Lin-Fu Liang Lin-Fu Liang Jiadong Sun Jiadong Sun Han Sun Han Sun Yue-Wei Guo Yue-Wei Guo Hong Wang Hong Wang Uncommon Polyoxygenated Sesquiterpenoids from South China Sea Soft Coral Lemnalia flava American Chemical Society 2019 13 C NMR data calculation South China Sea Lemnalia flava chemical investigation Coral Lemnalia flava neolemnane-type sesquiterpenoid time-dependent density nardosinane-type sesquiterpenoids X-ray diffraction analysis spectroscopic data analyses Plausible biogenetic pathways chemical reactions NMR analysis Uncommon Polyoxygenated Sesquiterpenoids dichroism calculation bicyclic skeleton 2019-02-14 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Uncommon_Polyoxygenated_Sesquiterpenoids_from_South_China_Sea_Soft_Coral_Lemnalia_flava/7792226 A detailed chemical investigation of the Chinese soft coral Lemnalia flava yielded four new nardosinane-type sesquiterpenoids (<b>1</b>–<b>4</b>), one new neolemnane-type sesquiterpenoid (<b>5</b>), and one new sesquiterpenoid with an uncommon 6/9 fused bicyclic skeleton (<b>6</b>), together with two known related compounds (<b>7</b> and <b>8</b>). The structures and absolute configurations of <b>1</b>–<b>8</b> were determined on the basis of extensive spectroscopic data analyses, X-ray diffraction analysis, chemical reactions, and computer-assisted structural elucidation including <sup>13</sup>C NMR data calculation, residual dipolar coupling based NMR analysis, and time-dependent density functional theoryelectronic circular dichroism calculation. Plausible biogenetic pathways of two uncommon sesquiterpenoids (<b>4</b> and <b>6</b>) were proposed.