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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
Elsevier Science
Year
2002
Tongue
French
Weight
86 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

πŸ“œ SIMILAR VOLUMES

An Efficient Synthesis of [(Tosylamino)a
An Efficient Synthesis of [(Tosylamino)alkyl]naphthalenols by Nucleophilic Addition of Naphthalen-2-ol with N-Tosyl Imines Using Boron Trifluoride Etherate as Catalyst
✍ Biswanath Das; Cheruku Ravindra Reddy; Chava Sindhu; Duddukuri Nandan Kumar; Mar πŸ“‚ Article πŸ“… 2011 πŸ› John Wiley and Sons 🌐 German βš– 124 KB πŸ‘ 1 views

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