A highly stereoselective in vitro cyclization of dolabellatriene diterpenes into novel dolastadienes

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1549-1556

  Jenny, Luzi ^a   Borschberg, Hans Jürg ^a   Acklin, Pierre ^b  

^a ETH ZURICH   (Switzerland)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; DOLASTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; GAS LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030060069     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01000-9     Document Type: Article

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26. 12
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42. 18
43. 16 of several of these systems are fully consistent with the experimental results, namely that these compounds prefer the C-anti ground state conformation.
44. 2-hybridized C(11) was shown to adopt the C-syn conformation as well: Williams, D.R.; Coleman, P.J.; Nevill, C.R.; Robinson, L.A. Tetrahedron Lett. 1993, 34, 7895-7898.
45. 3-catalyzed cyclization the observed 6:1-product ratio of subsequently rearranged dolastanes correlated well with the calculated low energy states: Williams, D.R.; Coleman, P.J. Tetrahedron Lett. 1995, 36, 39-42. In the case of a vaguely similar cyclization of the 11-membered diene lactone (E,E)-suspensolide the observed product distribution (1:2.3) very closely reflected the calculated equilibrium (1:2.1) of the two conformers of lowest energy in the starting material: Battiste, M.A.; Strekowski, L.; Coxon, J.M.; Wydra, R.L.; Harden, D.B. Tetrahedron Lett. 1991, 32, 5303-5304.
46. 3-catalyzed cyclization the observed 6:1-product ratio of subsequently rearranged dolastanes correlated well with the calculated low energy states: Williams, D.R.; Coleman, P.J. Tetrahedron Lett. 1995, 36, 39-42. In the case of a vaguely similar cyclization of the 11-membered diene lactone (E,E)-suspensolide the observed product distribution (1:2.3) very closely reflected the calculated equilibrium (1:2.1) of the two conformers of lowest energy in the starting material: Battiste, M.A.; Strekowski, L.; Coxon, J.M.; Wydra, R.L.; Harden, D.B. Tetrahedron Lett. 1991, 32, 5303-5304.