Gold(I)-Catalyzed Cyclizations of Silyl Enol Ethers: Application to the Synthesis of (+)-Lycopladine A

In control: Gold(I)‐catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)‐lycopl...

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Published inAngewandte Chemie International Edition Vol. 45; no. 36; pp. 5991 - 5994
Main Authors Staben, Steven T., Kennedy-Smith, Joshua J., Huang, David, Corkey, Britton K., LaLonde, Rebecca L., Toste, F. Dean
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.09.2006
WILEY‐VCH Verlag
Wiley
Subjects
Alkadienes - chemistry
alkaloids
Alkynes - chemistry
carbocyclization
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
Ethers - chemistry
gold
Gold - chemistry
homogeneous catalysis
Molecular Structure
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
silyl enol ethers
Stereoisomerism
carbocyclization
ALPHA,BETA-UNSATURATED KETONES
alkaloids
STEREOCHEMISTRY
EFFICIENT SYNTHESIS
PLATINUM
CARBONYL-COMPOUNDS
ENANTIOSELECTIVE CONSTRUCTION
MOLECULES
gold
homogeneous catalysis
GOLD-CATALYZED CYCLOISOMERIZATION
CYCLOPENTENE ANNULATION
silyl enol ethers
(-)-CUBEBOL
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Summary:In control: Gold(I)‐catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)‐lycopladine A that takes advantage of the orthogonal reactivity of AuI and Pd0 towards unsaturated iodides (see scheme).
Bibliography:ArticleID:ANIE200602035
ark:/67375/WNG-P8K6713S-X
We gratefully acknowledge the University of California, Berkeley, NIHGMS (R01 GM073932-01), Merck Research Laboratories, Bristol-Myers Squibb, Amgen Inc., DuPont, GlaxoSmithKline, Eli Lilly & Co., Pfizer, AstraZeneca, and Roche for financial support. J.J.K.-S. thanks Eli Lilly & Co. for a graduate fellowship. We thank Lauren A. Young for the preparation of tributylallenylstannane.
istex:E666CB7DF4304C1E1F1377B0BD7ACEBFFC7EFF3B
We gratefully acknowledge the University of California, Berkeley, NIHGMS (R01 GM073932‐01), Merck Research Laboratories, Bristol‐Myers Squibb, Amgen Inc., DuPont, GlaxoSmithKline, Eli Lilly & Co., Pfizer, AstraZeneca, and Roche for financial support. J.J.K.‐S. thanks Eli Lilly & Co. for a graduate fellowship. We thank Lauren A. Young for the preparation of tributylallenylstannane.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200602035