The synthesis of 13-spiro-substituted protoberberines via the tandem addition - Cyclisation reaction of 3-methoxyphthalide anions to 3,4-dihydroisoquinolines

Synlett

Volumn , Issue 4, 1998, Pages 387-388

  Wairener, Ronald N ^a   Liu, Ligong ^a   Russell, Richard A ^b   Tiekink, Edward R T ^c  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

^c UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001995935     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (7)

1. a) Marsden, R.; MacLean, D. B. Can. J. Chem. 1984, 62, 1392-1399;
2. b) Marsden, R.; MacLean, D. B. Tetrahedron Lett. 1983, 24, 2063-2066.
3. Warrener, R. N.; Liu, L.; Russell, R. A. unpublished results.
4. Mitchell, A. S.; Russell, R. A. Tetrahedron 1995, 5207-5236.
5. 13C NMR δ: 187.35, 162.67, 162.02, 148.20, 147.52, 134.97, 134.16, 132.23, 130.57, 130.01, 129.37, 129.35, 129.07, 128.95, 127.02, 126.25, 125.66, 124.27, 111.62, 110.02, 91.32, 66.19, 55.80, 55.71, 37.10, 29.54, 24.07.
6. w = 0.042 (sigma weights). Atomic coordinates, bond lengths and angles, and thermal parameters for the three structures have been deposited at the Cambridge Crystallographic Data Centre (CCDC).
7. For clarity we have illustrated the formation of only the enantiomer derived from the (13aS) precursor, however all reactions were conducted at the racemic level.