Palladium-catalyzed bisdiene carbocyclizations: Cycloisomerizations of bisdienes bearing an ester substituent

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5003-5006

  Takacs, James M ^a   Jaber, Mohamad R ^a   Strakhov, Alexander V ^a   Athalye, Rajan V ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PALLADIUM;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; ISOMERISM; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032500001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00979-4     Document Type: Article

References (21)

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13. (13) Takacs, J. M.; Chandramouli, S. V.; Shoemaker, R. Tetrahedron Lett. 1994, 35, 9161-4.
14. (14) Takacs, J. M.; Chandramouli, S. V. Tetrahedron Lett. 1994, 35, 9165-8.
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16. (16) For another example wherein an acyl substituent strongly influences the course of a catalytic palladium-mediated carbocyclization, see: Trost, B. M.; Grese, T. A. J. Org. Chem. 1992, 57, 686-97.
17. (17) The diastereomeric purity of the cyclized product (>90 %) seems to depend, at least in part, on the E:Z isomeric purity of the starting bisdiene.
18. (18) Tenaglia, A.; Brun, P.; Waegell, B. Tetrahedron Lett. 1985, 26, 3571-4.
19. (19) In comparison, the trans vinyl hydrogens within the butadienyl side chain of 3 exhibit a 15 Hz coupling constant and an approximate 0.5 % nOe.
20. a,b = 15.9 Hz.
21. (21) The minor component is tentatively assigned as the diastereomer that is epimeric at the 4-position of the cyclohexanol core in 11.