Synthesis of a phenolic analog of aphidicolin. Diminished stereoselection in intramolecular 6-exo Heck reactions of substrates having a hydrocarbon tether

Synlett

Volumn , Issue 12, 1997, Pages 1469-1471

  Abelman, Matthew M ^a,b   Kado, Noriyuki ^a,c   Overman, Larry E ^a   Sarkar, Achintya K ^a,d  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c Abbott Japan Co Ltd   (Japan)

^d PRESIDENCY UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001906301     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1066     Document Type: Article

References (17)

1. (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross Coupling Reactions; Stang, P. J. and Diederick, F., Eds.; Wiley-VCH: Weinheim, 1997.
2. (b) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross Coupling Reactions; Stang, P. J. and Diederick, F., Eds.; Wiley-VCH: Weinheim, 1997.
3. For reviews, see: Overman, L. E. Pure Appl. Chem. 1994, 66, 1423 and reference 2b.
4. Abelman, M. M.; Overman, L. E.; Tran, V. D. J. Am. Chem. Soc. 1990, 112, 6959.
5. (a) Original isolation: Brundret, K. M.; Dalziel, W.; Hesp, B.; Jarvis, J. A. J.; Neidle, S. J. Chem. Soc., Chem. Commun. 1972, 1027.
6. (b) Mechanism of DNA polymerase α inhibition: Sheaff, R.; Ilsley, D.; Kuchta, R. Biochemistry 1991, 30, 8590.
7. (a) First total syntheses: Trost, B. M.; Nishimura, Y.; Yamamoto, K.; McElvain, S. S. J. Am. Chem. Soc. 1979, 101, 1328.
8. McMurry, J. E.; Andrus, A.; Ksander, G. M.; Musser, J. H.; Johnson, M. A. J. Am. Chem. Soc. 1979, 101, 1330.
9. (b) Recent review of tetracyclic diterpene total synthesis: Goldsmith, D. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 8, Chapter 1.
10. 13C, IR, and mass spectrometric analysis. The elemental composition of analytical samples of new compounds was confirmed by combustion analysis or high-resolution mass spectrometry. Yields refer to isolated, purified products.
11. Aryl diiodide 11 was prepared from 3-methoxybenzaldehyde by the sequence summarized in eq 1. (Chemical Equation Presented)
12. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
13. Corey, E. J.; Tius, M. A.; Das, J. J. Am. Chem. Soc. 1980, 102, 1742.
14. That stereoselectivity would be high in addition to the C(16) exo methylene group of this diene was anticipated: Lupi, A.; Patamia, M.; Bettolo, R. M. Helv. Chim. Acta 1988, 71, 872.
15. 3, M, 1%), 199 (44%), 149 (41%), 73 (100%).
16. Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328.
17. 1H NMR nOe experiments.