Cyclohexenone annelation by alkylidene C-H insertion: Synthesis of oxo-T-cadinol

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 2081-2084

  Taber, Douglass F ^a   Christos, Thomas E ^a   Hodge, C Nicholas ^b  

^a UNIVERSITY OF DELAWARE   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; ALKYLIDENES; ALLYL BROMIDE; C-H INSERTION; CARBENES; CYCLOPENTENES; DEBENZYLATION; DIAZOMETHANES; OZONOLYSIS; T-CADINOL; TRIMETHYLSILYL;

HYDROCARBONS; OZONE;

KETONES;

CALCIUM ANTAGONIST; CYCLOHEXANE DERIVATIVE; OXO T CADINOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029877743     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951949k     Document Type: Article

References (25)

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22. While this work was in progress, a report (ref 3h) of such an alkylidene insertion appeared.
23. 1H spectrum of the natural product was kindly provided by P. M. Zygmunt.
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25. Simulation conditions: 1 fs timestep, dielectric constant ∈ = 80, temperature = 2500 °C, minimize every ps using, in sequence, steepest descent (200 steps or RMSD < 1.00 kcal/A), conjugate gradient (500 steps or RMSD < 0.1 kcal/A), and quasi-Newton-Raphson (1000 steps or RMSD < 0.01 kcal/A). The total simulation time of 100 ps requires a total cpu time of 22 h 55 min running in parallel on four R8000 Silicon Graphics processors. The input files are available as supporting information.