Investigation of an unusual rearrangement

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 21-24

  Smith, David B ^a   Elworthy, Todd R ^a   Morgans Jr , David J ^a   Nelson, Janis T ^b   Patterson, John W ^a   Vasquez, Alfredo ^a   Waltos, Ann Marie ^a  

^a Syntex Research Institute of Organic Chemistry   (United States)

^b ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MYCOPHENOLIC ACID; MYCOPHENOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030032669     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02101-9     Document Type: Article

References (9)

1. Several manuscripts concerning the details of the synthesis and biological properties of mycophenolic acid analogues are in progress and will appear in due course. For previous work from these laboratories, see: Nelson, P. H.; Eugui, E.; Wang, C. C.; Allison, A. C. J. Med. Chem. 1990, 33, 833.
2. Claisen, L. Chem. Ber. 1912, 45, 3157.
3. a) Fukuyama, T.; Tangqing, L.; Peng, G. Tetrahedron Lett. 1994, 35, 2145.
4. b) Karanewsky, D. S.; Kishi, Y. J. Org. Chem. 1976, 41, 3026.
5. c) Vdovtsova, E. A. Zh. Org. Khim. 1969, 5, 498.
6. Substrates 3a-e were prepared via Mitsunobu coupling (review: Mitsunobu, O. Synthesis, 1981, 1) of the appropriate allylic alcohol with phenol 5. For an efficient preparation of 5, see: Patterson, J. W. Tetrahedron 1993, 49, 4789.
7. 13C NMR, IR, MS, UV and combustion analysis.
8. 4 C 68.69, H 6.92. Found: C 68.95, H 6.97.
9. 3-5 we adapted the method of Patterson given in reference 4.