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Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2017

Electronic Supporting Information

Construction of the oxaphenalene skeletons of mansonone F derivatives through C-H bond functionalization and their evaluation for anti-proliferative activities

Hua-Ting ‡, Du-Chao Zhou‡, - , Lian , -Fen Yao, Shi-Liang *, Hong-Gen Wang, Zhi- Huang, Lian-Quan Gu

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People’sRepublic of China

‡ Contributed equally to this work

*To whom correspondence should be addressed. Tel.: 8620-39943052,

Fax.: 8620-39943056, e-mail: [email protected].

S1 Table of contents

1H NMR,13C NMR and HRMS spectrum of the intermediates 2a~2f...... S3

1H NMR,13C NMR spectra of the intermediates 9, 10, 11 and 12……………………....S12

1H NMR,13C NMR, HRMS spectra，IR spectra and HPLC of the target compounds.. .S16

HMQC, HMBC and NOSEY spectra of compound 17.…...... …...... …...... S92

S2 1H NMR spectra of 2a

13C NMR spectra of 2a

S3 HRMS spectrum of 2a

1H NMR spectra of 2b

S4 13C NMR spectra of 2b

HRMS spectrum of 2b

S5 1H NMR spectra of 2c

13C NMR spectra of 2c

S6 HRMS spectrum of 2c

1H NMR spectra of 2d

S7 13C NMR spectra of 2d

HRMS spectrum of 2d

S8 1H NMR spectra of 2e

13C NMR spectra of 2e

S9 HRMS spectrum of 2e

1H NMR spectra of 2f

S10 13C NMR spectra of 2f

HRMS spectrum of 2f

S11 1H NMR spectra of 9

13C NMR spectra of 9

S12 1H NMR spectra of 10

13C NMR spectra of 10

S13 1H NMR spectra of 11

13C NMR spectra of 11

S14 1H NMR spectra of 12

13C NMR spectra of 12

S15 HRMS spectrum of 12

1H NMR spectra of 3a

S16 13C NMR spectra of 3a

HRMS spectrum of 3a

S17 IR spectra of 3a

HPLC profile of 3a

S18 1H NMR spectra of 4a

13C NMR spectra of 4a

S19 HRMS spectrum of 4a

IR spectra of 4a

S20 HPLC profile of 4a

1H NMR spectra of 5a

S21 13C NMR spectra of 5a

HRMS spectrum of 5a

S22 IR spectra of 5a

HPLC profile of 5a

S23 1H NMR spectra of 6a

13C NMR spectra of 6a

S24 HRMS spectrum of 6a

IR spectra of 6a

S25 HPLC profile of 6a

1H NMR spectra of 7a

S26 13C NMR spectra of 7a

HRMS spectrum of 7a

S27 IR spectra of 7a

HPLC profile of 7a

S28 1H NMR spectra of 3b

、 13C NMR spectra of 3b

S29 HRMS spectrum of 3b

IR spectra of 3b

S30 HPLC profile of 3b

1H NMR spectra of 4b

S31 13C NMR spectra of 4b

HRMS spectrum of 4b

S32 IR spectra of 4b

HPLC profile of 4b

S33 1H NMR spectra of 5b

13C NMR spectra of 5b

S34 HRMS spectrum of 5b

IR spectra of 5b

S35 HPLC profile of 5b

1H NMR spectra of 6b

S36 13C NMR spectra of 6b

HRMS spectrum of 6b

S37 IR spectra of 6b

HPLC profile of 6b

S38 1H NMR spectra of 7b

13C NMR spectra of 7b

S39 HRMS spectrum of 7b

IR spectra of 7b

S40 HPLC profile of 7b

1H NMR spectra of 3c

S41 13C NMR spectra of 3c

HRMS spectrum of 3c

S42 IR spectra of 3c

HPLC profile of 3c

S43 1H NMR spectra of 4c

13C NMR spectra of 4c

S44 HRMS spectrum of 4c

IR spectra of 4c

S45 HPLC profile of 4c

1H NMR spectra of 5c

S46 13C NMR spectra of 5c

HRMS spectrum of 5c

S47 IR spectra of 5c

HPLC profile of 5c

S48 1H NMR spectra of 6c

13C NMR spectra of 6c

S49 HRMS spectrum of 6c

IR spectra of 6c

S50 HPLC profile of 6c

1H NMR spectra of 7c

S51 13C NMR spectra of 7c

HRMS spectrum of 7c

S52 IR spectra of 7c

HPLC profile of 7c

S53 1H NMR spectra of 3d

13C NMR spectra of 3d

S54 HRMS spectrum of 3d

IR spectra of 3d

S55 HPLC profile of 3d

1H NMR spectra of 6d

S56 13C NMR spectra of 6d

HRMS spectrum of 6d

S57 IR spectra of 6d

HPLC profile of 6d

S58 1H NMR spectra of 7d

13C NMR spectra of 7d

S59 HRMS spectrum of 7d

IR spectra of 7d

S60 HPLC profile of 7d

1H NMR spectra of 3e

S61 13C NMR spectra of 3e

HRMS spectrum of 3e

S62 IR spectra of 3e

HPLC profile of 3e

S63 1H NMR spectra of 6e

13C NMR spectra of 6e

S64 HRMS spectrum of 6e

IR spectra of 6e

S65 HPLC profile of 6e

1H NMR spectra of 7e

S66 13C NMR spectra of 7e

HRMS spectrum of 7e

S67 IR spectra of 7e

HPLC profile of 7e

S68 1H NMR spectra of 3f

13C NMR spectra of 3f

S69 HRMS spectrum of 3f

IR spectra of 3f

S70 HPLC profile of 3f

1H NMR spectra of 6f

S71 13C NMR spectra of 6f

HRMS spectrum of 6f

S72 IR spectra of 6f

HPLC profile of 6f

S73 1H NMR spectra of 7f

13C NMR spectra of 7f

S74 HRMS spectrum of 7f

IR spectra of 7f

S75 HPLC profile of 7f

1H NMR spectra of 13

S76 13C NMR spectra of 13

HRMS spectrum of 13

S77 IR spectra of 13

HPLC profile of 13

S78 1H NMR spectra of 14

13C NMR spectra of 14

S79 HRMS spectrum of 14

IR spectra of 14

S80 HPLC profile of 14

1H NMR spectra of 16a

S81 13C NMR spectra of 16a

HRMS spectrum of 16a

S82 IR spectra of 16a

HPLC profile of 16a

S83 1H NMR spectra of 16b

13C NMR spectra of 16b

S84 HRMS spectrum of 16b

IR spectra of 16b

S85 HPLC profile of 16b

1H NMR spectra of 16c

S86 13C NMR spectra of 16c

HRMS spectrum of 16c

S87 IR spectra of 16c

HPLC profile of 16c

S88 1H NMR spectra of 16d

13C NMR spectra of 16d

S89 HRMS spectrum of 16d

IR spectra of 16d

S90 HPLC profile of 16d

1H NMR spectra of 17

S91 13C NMR spectra of 17

HMBC spectra of 17

S92 HMQC spectra of 17

NOESY spectra of 17

S93 HRMS spectrum of 17

IR spectra of 17

S94 HPLC profile of 17

S95