Journal
TETRAHEDRON LETTERS
Volume 43, Issue 39, Pages 6929-6932Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)01627-1
Keywords
aureol; arenarol; marine natural product; rearrangement; domino reaction
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A novel marine natural product, (+)-aureol (1), was efficiently synthesized starting from the cis-fused decalin derivative 4. The synthetic method features boron trifluoride etherate-promoted rearrangement/cyclization reaction of (+)-arenarol (2) to form (+)-aureol (1) with complete stereoselectivity in high yield. (+)-Arenarol (2) was prepared in an alternative and more efficient manner employing salcomine oxidation protocol. (C) 2002 Elsevier Science Ltd. All rights reserved.
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