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

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 allylpall...

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Published inHelvetica chimica acta Vol. 84; no. 2; pp. 416 - 430
Main Authors Oppolzer, Wolfgang, Flachsmann, Felix
Format Journal Article
LanguageEnglish
Published Basel Verlag Helvetica Chimica Acta 28.02.2001
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PI-ALLYLPALLADIUM
REAGENTS
ACTIVE ACYLATION CATALYST
ENE-TYPE CYCLIZATIONS
TRIFLUOROMETHANESULFONATE
ERYTHRODIENE
STEREOSELECTIVE PREPARATION
CERIUM(III) CHLORIDE
SPIROJATAMOL
ZINC
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Abstract 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.
AbstractList 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 Et,Zn 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 allylzincation of a methyl ketone. Both reactions showed the same stereochemical preference. yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.
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.
Author Flachsmann, Felix
Oppolzer, Wolfgang
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  givenname: Felix
  surname: Flachsmann
  fullname: Flachsmann, Felix
  email: felix.flachsmann@givaudan.com
  organization: Département de Chimie Organique, Université de Genève, CH-1211 Genève 4
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Issue 2
Keywords PI-ALLYLPALLADIUM
REAGENTS
ACTIVE ACYLATION CATALYST
ENE-TYPE CYCLIZATIONS
TRIFLUOROMETHANESULFONATE
ERYTHRODIENE
STEREOSELECTIVE PREPARATION
CERIUM(III) CHLORIDE
SPIROJATAMOL
ZINC
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Deceased March 15, 1996.
Parts of this work have been published in preliminary form [7].
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Wiley
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SSID ssj0009907
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Snippet Two spirobicyclic sesquiterpenoids, (−)‐erythrodiene (1) and (+)‐7‐epispirojatamol (30), were synthesized in enantiomerically pure form via an intramolecular...
Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30),were synthesized in enantiomerically pure form via an intramolecular...
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StartPage 416
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Synthesis of (−)-Erythrodiene and (+)-7-Epispirojatamol via Intramolecular Pd-Catalyzed Allylzincation
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