Double annulation route to fused bicyclic compounds with three contiguous quaternary centers

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1583-1586

  Grossman, Robert B ^a   Skaggs, Aaron J ^a   Kray, Arlene E ^a   Patrick, Brian O ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000174098     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990935o     Document Type: Article

References (26)

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20. -1.
21. Although the yields are low or moderate in some cases, in no case does GC-MS analysis of the crude reaction mixture show any evidence for products with molecular weights identical or close to those of the isolated products.
22. The large R value was due to rather large thermal motion, but nothing was found which would have cast doubt on the stereochemistry.
23. A subsequent X-ray study of this compound revealed the possibility of a second crystal form. Details will be presented in a future publication. Brock, C. P.; Patrick, B. O.; Grossman, R. B.; Skaggs, A. J. Unpublished results.
24. a(conj. acid) ≈ 20] . Such an elementary step is not expected to be very exothermic, and hence the Hammond postulate suggests that the TS should resemble the product.
25. ax seems to be due to dipolar interactions between the axial CN groups and the enolates, not steric interactions.
26. However, the imidate precursors to lactones 4 could not be equilibrated to the corresponding trans-decalins, even after the reaction mixtures were allowed to stir with excess base for extended periods of time.