Abstract
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 TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.
Original language | English |
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Pages (from-to) | 2572-2576 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 69 |
Issue number | 12 |
DOIs | |
Publication status | Published - Mar 25 2013 |
Keywords
- Potassium vinyltrifluoroborate
- Pterosin A
- Suzuki-Miyaura reaction
- Vinylation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry