Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

A practical synthesis of (+/-)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCI, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCI, oxidation of the secondary alcohol, and desilylation with TBAF. (C) 2013 Elsevier Ltd. All rights reserved.