A scalemic synthesis of the scopadulcic acid skeleton. II: Ring-D formation via regiospecific intramolecular aldol and alkylation reactions

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8463-8466

  Tagat, Jayaram R ^b   Puar, Mohindar S ^a   McCombie, Stuart W ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

SCOPADULCIC ACID B;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 16144364258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01948-X     Document Type: Article

References (8)

1. 1. Tagat, J. R.; McCombie, S. W.; Puar, M. S. Tetrahedron Lett. preceding paper in this issue.
2. 2 a). Hirsch, J. A.; Wang, X. L. Synth. Comm. 1982, 12, 333.
3. b). Goldsmith, D. J.; Dickinson, C. M.; Lewis, A. J. Heterocycles 1987, 25, 291.
4. 3. The C-9 unsubstituted abietenone forms dienol derivatives rapidly (1-4h) and their oxidation is also a quick reaction proceeding stereoselectively to 7α-hydroxy enone in high yield (see ref.1).
5. 4. a). Suryavanshi, S. N.; Fuchs, P. L. Tetrahedron Lett. 1981, 22, 4201.
6. b). Suryavanshi, S. N.; Fuchs, P. L. J. Org. Chem. 1986, 51, 902.
7. 5. The 7α-trimethylsilyloxy enone aldehyde 23 spontaneously cyclizes to 24 which was reduced to 25: (matrix presented)
8. +) requires 329.2117; Found: 329.2110.