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

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

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 417 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01254-1

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✦ Synopsis

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 (E,Z)-farnesyl acetate, synthesized from nerol, has been carried out. This process stops at the first cyclization indicating that an E configuration of the D 6 double bond is needed for the second cyclization to occur. The results are discussed in comparison with previous knowledge on the related Re(VII) polycyclization of polyenic bis-homoallylic alcohols.

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RuO4-promoted syn-oxidative polycyclizat

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

✍ Giuseppe Bifulco; Teresa Caserta; Luigi Gomez-Paloma; Vincenzo Piccialli 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 242 KB

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

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.