Platinum- and gold-catalyzed rearrangement reactions of propargyl acetates: Total syntheses of (-)-α-cubebene, (-)-cubebol, sesquicarene and related terpenes

Chemistry - A European Journal

Volumn 12, Issue 11, 2006, Pages 3006-3019

  Fürstner, Alois ^a   Hannen, Peter ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Carbenes; Gold; Natural products; Platinum; Terpene

Indexed keywords

GOLD; HYDROCARBONS; HYDROGENATION; OXIDATION; PLATINUM; SOLVENTS; STEREOCHEMISTRY; SUBSTRATES; TOLUENE; TRANSITION METALS;

CARBENES; ELECTROPHILIC CYCLOPROPYL; HYDROBORATION; NATURAL PRODUCTS; PROPARGYL ACETATES; TERPENE;

CATALYSTS;

EID: 33645688330     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501299     Document Type: Article

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156. Although two consecutive acetyl migrations via intermediates such as B and C could also explain the formation of the allenyl acetate 34, previous literature reports generally assume a [3,3]-sigmatropic pathway for reactions of this type, see ref. [48].
157. 6.
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161. Other conceivable methods for the dehydration of alcohol 37 gave much more complex product mixtures.
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163. 3N as hydride sources led to somewhat lower yields in this particular transformation (60 and 41 %, respectively).
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165. It is worth mentioning that isosequicarene, a natural product isolated from Haplopappus tenuisectus, shows this particular configuration at C-7 but has a 3-carene rather than a 2-carene core, see: T. Uyehara, J. Yamada, T. Kato, F. Bohlmann, Bull. Chem. Soc. Jpn. 1985, 58, 861-867.