A practical synthesis of the milbemycin SB-201561

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4811-4814

  Andrews, Ian P ^a   Dorgan, Roderick J J ^a   Harvey, Timothy ^a   Hudner, Joseph F ^a   Hussain, Nigel ^a   Lathbury, David C ^a   Lewis, Norman J ^a   Macaulay, Graham S ^a   Morgan, David O ^a   Stockman, Robert ^a   White, Charles R ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTHELMINTIC AGENT; SB 201561; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 15844381949     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00943-4     Document Type: Article

References (7)

1. 1. Davies H. G., Green R. H., Chem. Soc. Rev., 1991, 20, 211-269 and 271-339
2. 2. Baker G. H., Blanchflower S. E., Dorgan R. J. J., Morgan D. O., Shelly D. R, Eur. Pat. App., EP 421,568, 10/5/91
3. 3. Hood J. D., Banks R. M., Brewer M. D., Fish J. P., Manger B. R., Poulton M. E., J. Antibiotics, 1989, 42, 1593-98
4. 4. Tidwell T. T., Org. React., 1990, 39, 297-572
5. 5. Baker G. H., Dorgan R. J. J., Hussain N., Macaulay G. S., Morgan D. O., Tetrahedron Letters, 1994, 35, 2381-84
6. 6. The exact mechanism of this remarkable transformation is not totally clear, however, if the reaction is carried out in the presence of triethylamine a rather unstable product is isolated which was tentatively assigned as (11). (formula presented)
7. 7. (10) was prepared from the corresponding Aldol product, using the following sequence: (formula presented) It was later found that use of the dianion derived from (12) gave comparable yields to those obtained using (10). Initial attempts at using the corresponding ketone enolate derived from (13) gave poorer yields owing to competitive lactone deprotonation. (formula presented)