Scientific article

Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamol via Intramolecular Pd-Catalyzed Allylzincation

Published inHelvetica chimica acta, vol. 84, no. 2, p. 416-430
Publication date2001-02-28
First online date2001-02-23

Two spirobicyclic sesquiterpenoids, (−)-erythrodiene (1) and (+)-7-epispirojatamol (30), were synthesized in enantiomerically pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et2Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)2]/Bu3P (1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin, 30 was formed via a novel intramolecular allyl zincation of a methyl ketone. Both reactions showed the same stereochemical preference, yielding the spirobicyclic products in 95 : 5 and 4 : 1 diastereoisomer ratios, respectively.

Citation (ISO format)
VON OPPOLZER, Wolfgang, FLACHSMANN, Félix. Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamol via Intramolecular Pd-Catalyzed Allylzincation. In: Helvetica chimica acta, 2001, vol. 84, n° 2, p. 416–430. doi: 10.1002/1522-2675(20010228)84:2<416::AID-HLCA416>3.0.CO;2-K
Main files (1)
Article (Published version)
ISSN of the journal0018-019X

Technical informations

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