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An Efficient Synthesis of (+)-Aureol via Boron Trifluoride Etherate-Promoted Rearrangement of (+)-Arenarol.

✍ Scribed by Masahiko Nakamura; Akiyuki Suzuki; Mari Nakatani; Takamasa Fuchikami; Munenori Inoue; Tadashi Katoh


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
33
Category
Article
ISSN
0931-7597

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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 stereoselectivit

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Tosylamino)alkyl]naphthalenols have efficiently been synthesized by nucleophilic addition of naphthalen-2-ol with N-tosyl imines (derived from both aromatic and aliphatic aldehydes) in the presence of BF 3 β€’ OEt 2 as a catalyst at room temperature. The products are formed within 5 -9 h in high yield