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Synlett 2013; 24(5): 615-618
DOI: 10.1055/s-0032-1318310
DOI: 10.1055/s-0032-1318310
letter
Total Synthesis of (±)-Spirobenzofuran
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.
Key words
spirobenzofuran - semipinacol rearrangement - trimethylaluminium - total synthesis - sesquiterpenoidSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- 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.