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S1 Regiodivergent synthesis of trisubstituted furans through Tf 2 O- catalyzed Friedel-Crafts acylation: a tool for access to tetrahydrofuran lignan analogues Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli, and Simona Zuppolini Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario di Monte S. Angelo, via Cinthia 4, I-80126 Naples, Italy. Fax: +39 081 6741393; Tel: +39 081 674162; E-mail: [email protected]; [email protected] . SUPPORTING INFORMATION Table of contents 1D NMR Spectra: 1 H and 13 C NMR of compounds 3a-e, 4a-e, 5,7-9……………..……….pg. S2-S15 2D NMR Spectra: HMQC of compound 3a…………………………………………………. pg. S16 HMBC of compound 3a………………………………………………… pg. S16 HSQC of compound 4a..…………………………………………………. pg. S17 HMBC of compound 4a..………………………………………………….pg. S17 HMBC of compound 5…………………………………………………….pg. S18 COSY of compound 9…………………………………………………… pg. S18 HMBC of compound 9………………………………………………….. pg. S19 NOESY of compound 9…………………………………………………. pg. S19 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2011

Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

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Page 1: Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

S1

Regiodivergent synthesis of trisubstituted furans through Tf2O-

catalyzed Friedel-Crafts acylation: a tool for access to

tetrahydrofuran lignan analogues

Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli, and Simona Zuppolini

Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario di Monte

S. Angelo, via Cinthia 4, I-80126 Naples, Italy. Fax: +39 081 6741393; Tel: +39 081 674162; E-mail:

[email protected]; [email protected].

SUPPORTING INFORMATION

Table of contents

1D NMR Spectra:

1H and

13C NMR of compounds 3a-e, 4a-e, 5,7-9……………..……….pg. S2-S15

2D NMR Spectra:

HMQC of compound 3a…………………………………………………. pg. S16

HMBC of compound 3a………………………………………………… pg. S16

HSQC of compound 4a..…………………………………………………. pg. S17

HMBC of compound 4a..………………………………………………….pg. S17

HMBC of compound 5…………………………………………………….pg. S18

COSY of compound 9…………………………………………………… pg. S18

HMBC of compound 9………………………………………………….. pg. S19

NOESY of compound 9…………………………………………………. pg. S19

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

Page 2: Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

Page 3: Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

Page 4: Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

Page 5: Regiodivergent synthesis of trisubstituted furans through Tf O- … · 2011. 11. 3. · Daniela Comegna,* Marina DellaGreca,* M. Rosaria Iesce, Lucio Previtera, Armando Zarrelli,

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

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Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011