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RuO4-promoted syn-oxidative polycyclization of isoprenoid polyenes: a new stereoselective cascade process

✍ Scribed by Giuseppe Bifulco; Teresa Caserta; Luigi Gomez-Paloma; Vincenzo Piccialli

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 242 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02304-3

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✦ Synopsis

Isoprenoid polyenes farnesyl acetate, geranylgeranyl acetate and squalene undergo oxidative polycyclization to bis-, tris-, and penta-tetrahydrofurane products, respectively, in the presence of catalytic amounts of RuO 4 (from RuO 2 •2H 2 O) and NaIO 4 as primary oxidant. The stereochemistry of the bis-cyclization product was established as cis-threo-cis-threo through chemical methods and 2D-NMR experiments, and a cascade mechanism was proposed that explains the reactivity exhibited by all the related polyenes. A similarity with rhenium(VII) chemistry has emerged.

📜 SIMILAR VOLUMES

Corrigendum to “RuO4-promoted syn-oxidat

Corrigendum to “RuO4-promoted syn-oxidative polycyclization of isoprenoid polyenes: a new stereoselective cascade process”: [Tetrahedron Lett. 43 (2002) 9265]

✍ Giuseppe Bifulco; Teresa Caserta; Luigi Gomez-Paloma; Vincenzo Piccialli 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 140 KB

We regret that in Scheme 1, the configurations of C-2, C-3 and C-6 in compound 1, and C-3 and C-6 in 2 have been drawn in an erroneous way. The wrong and correct structures are shown.

RuO4-promoted oxidative polycyclization

RuO4-promoted oxidative polycyclization of isoprenoid polyenes. A further insight into the stereochemistry of the process

✍ Giuseppe Bifulco; Teresa Caserta; Luigi Gomez-Paloma; Vincenzo Piccialli 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 417 KB

Further studies on the RuO 4 -catalyzed oxidative polycyclization of isoprenoid polyenes have been carried out. The configuration of the tris-THF product from the oxidation of geranylgeranyl acetate has been determined by a combination of spectral and chemical correlation methods. The oxidation of (