Supporting Information. Organocatalytic Stereoselective Synthesis of Passifloricin A
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1 Supporting Information Organocatalytic Stereoselective Synthesis of Passifloricin A Pradeep Kumar,* a Menaka Pandey a, Priti Gupta a, Dilip D. Dhavale b a Division of Organic Chemistry, National Chemical Laboratory, Pune , India b Department of Chemistry, University of Pune, Pune , India *Corresponding Author: Telephone number: , Fax number: ; address: pk.tripathi@ncl.res.in Table of contents Sr. No. S-4 S-5 Contents 1 H and 13 C spectra of compound 8 1 H and 13 C spectra of compound 10 S-6 HPLC data of compound 24 S-7 S-8 S-9 1 H and 13 C spectra of compound 11 1 H and 13 C spectra of compound 12 1 H and 13 C spectra of compound 13 S1
2 S-10 S-11 S-12 S-13 S-14 S-15 S H and 13 C spectra of compound 16 1 H and 13 C spectra of compound 17 1 H and 13 C spectra of compound 19 1 H and 13 C spectra of compound 20 1 H and 13 C spectra of compound 20 1 H and 13 C spectra of compound 22 1 H spectra of compound 1 Experimental Section General Methods: All reactions were carried out under argon or nitrogen in oven-dried glassware using standard gas-light syringes, cannulas and septa. Solvents and reagents were purified and dried by standard methods prior to use. Optical rotations were measured at room temperature. IR spectra were recorded on an FT-IR instrument. 1 H S2
3 NMR spectra were recorded on 200 MHz, 300 MHz and 500 MHz and are reported in parts per million ( ) downfield relative to CDCl 3 as internal standard and 13 C NMR spectra were recorded at 50 MHz, 75 MHz and 125 MHz and assigned in parts per million ( ) relative to CDCl 3. Column chromatography was performed on silica gel ( and mesh) using a mixture of petroleum ether and ethyl acetate as the eluent. S3
4 S4
5 Fri4av500#004 Chlorof orm-d Chlorof orm-d Fri4av500# S5
6 S6
7 Chlorof orm-d Fri4av500# S7
8 S8
9 S9
10 16 16 S10
11 S11
12 S12
13 S13
14 S14
15 OTBS O O O 22 O S15
16 Fri4av500# S16
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