Claims
- 1. A sixteen-membered macrolide
having a side chain Z at C-8 of the macrolide wherein Z is selected from the group consisting of: hydrogen, —O—(CH2)n-cycloalkyl; —O—(CH2)n-heterocyclo; —O—(CH2)n-aryl; —O—(CH2)n—CH═CH-aryl; and —O—(CH2)n—CH═CH—CH2-aryl where n is 0-5; or a fused bicyclic compound where one of the cyclic components is a sixteen-membered macrolide and the other is a five- or six-membered heterocyclic moiety.
- 2. The macrolide as in claim 1 of the formula
- 3. The macrolide as in claim 2 wherein the 4-acyl or 4-sulfonyl group in mycarose is selected from the group consisting of isovaleryl; phenylacetyl; phenylthioacetyl; phenylsulfonylacetyl; 4-nitrophenylacetyl; 4-nitrophenylsulfonyl; and phenylethanesulfonyl.
- 4. The macrolide as in claim 2 wherein the aryl is selected from the group consisting of
- 5. The bicyclic compound of claim 1 of the formula
- 6. The bicyclic compound of claim 1 of the formula
- 7. The bicyclic compound of claim 1 of the formula
- 8. The bicyclic compound of claim 1 of the formula
- 9. The compound as in claim 5, 6, 7, or 8 wherein the aryl is selected from the group consisting of
- 10. The compound as in claim 5, 6, 7, or 8 wherein the 4-acyl or 4-sulfonyl group in mycarose is selected from the group consisting of isovaleryl; phenylacetyl; phenylthioacetyl; phenylsulfonylacetyl; 4-nitrophenylacetyl; 4-nitrophenylsulfonyl; and phenylethanesulfonyl.
- 11. A method of making a 8-hydroxy-9-oxo macrolide comprising converting a 9-oxo macrolide into a 8,9-silyl enolether and oxidizing the 8,9-silyl enolether to the 8-hydroxy-9-oxo macrolide.
- 12. A method of making a bicyclic compound wherein one of the cyclic components is a sixteen-membered macrolide and the other is a six-membered cyclic ether comprising
converting a 12-ene-14-hydroxymethyl-macrolide to a 12-ene-14-alkynylalkoxymethyl macrolide; and treating the 12-ene-14-alkynylalkoxymethyl macrolide with a trialkyl-tin-hydride.
- 13. A dihydroxylation method comprising
hydroxylating a 10-ene sixteen-membered macrolide to form a 10,11-dihydroxy macrolide.
- 14. A method of adding a nucleophile at C-12 of a 9-oxo-10-ene-12,13-epoxy sixteen-membered macrolide comprising
treating the macrolide with a transition metal catalyst in the presence of the nucleophile.
- 15. A method of making a 9-oxo-10-ene-12-hydroxy sixteen-membered macrolide comprising
treating a 9-oxo-11-ene-13-hydroxy macrolide with an epoxidizing agent to form a 11, 12-epoxide; and treating the epoxide with a base to make the 9-oxo-10-ene-12-hydroxy sixteen-membered macrolide.
Parent Case Info
[0001] This application asserts priority to U.S. Provisional Application No. 60/269,693 filed Feb. 17, 2001 entitled NOVEL SIXTEEN-MEMBERED MACROLIDES by inventors Leonard Katz and Gary Ashley; U.S. Provisional Application No. 60/251,338 filed Dec. 4, 2000 by inventors Leonard Katz and Gary Ashley; and U.S. Provisional Application No. 60/234,994 filed Sep. 25, 2000 entitled NOVEL MACROLIDES by inventors Leonard Katz and Gary Ashley, all of which are incorporated herein by reference.
Provisional Applications (3)
|
Number |
Date |
Country |
|
60251338 |
Dec 2000 |
US |
|
60269693 |
Feb 2001 |
US |
|
60234994 |
Sep 2000 |
US |