Synlett 2013; 24(5): 615-618
DOI: 10.1055/s-0032-1318310
letter
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Spirobenzofuran

Hang Su
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610 064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Ting Zhou
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610 064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
,
Bo Liu*
a   Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610 064, P. R. of China   Fax: +86(28)85413712   Email: chembliu@scu.edu.cn
b   Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200 032, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 12 January 2013

Accepted after revision: 04 February 2013

Publication Date:
20 February 2013 (online)


Abstract

Spirobenzofuran, embracing a cyclopentane-spirofused benzofuran carbon framework, was efficiently assembled via semipinacol rearrangement with Me3Al from 2,5-dimethoxy-4-methylacetophenone.

Supporting Information

 
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  • 23 Analytical Data 1H NMR (400 MHz, DMSO-d 6): δ = 8.66 (s, 1 H), 7.14 (d, J = 5.6 Hz, 1 H), 6.52 (s, 2 H), 5.79 (d, J = 5.6 Hz, 1 H), 2.83 (d, J = 18.8 Hz, A of AB, 1 H), 2.44 (d, J = 18.8 Hz, B of AB, 1 H), 2.34 (d, J = 18.4 Hz, A′ of A′B′, 1 H), 2.24 (d, J = 18.0 Hz, B′ of A′B′, 1 H), 2.07 (s, 3 H), 0.98 (s, 3 H), 0.85 (s, 3 H). 13C NMR (100 MHz, DMSO-d 6): δ = 216.2, 150.3, 148.9, 126.5, 123.8, 111.2, 111.0, 102.1, 59.2, 51.9, 42.7, 41.2, 24.6, 23.0, 16.3. IR (thin film): 3395, 1732, 1412, 1085, 923 cm–1. HRMS (ES+): m/z calcd for C15H18O4Na [M + Na]+: 285.1103; found: 285.1101.