Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.
Stereoselective syntheses of the C(1)-C(9) fragments 18 and 28 of amphidinolide C have been developed. The first-generation sequence involves a diastereoselective chelate-controlled [3 + 2]-annulation reaction of 6 and 7, while the second-generation synthesis involves an intramolecular hetero-Michael cyclization of 8.
Bates
Robert H
RH
Department of Chemistry, Scripps Florida, Jupiter, Florida 33458, USA.
Shotwell
J Brad
JB
Roush
William R
WR
D000818:Animals; D045744:Cell Line, Tumor; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D013237:Stereoisomerism; D013379:Substrate Specificity; D000097442:Amphidinolides
D018942:Macrolides; C429132:amphidinolide C; D000097442:Amphidinolides
J Am Chem Soc. 1976 May 12;98(10):3022-3
1262631
Org Lett. 2001 Jun 14;3(12):1949-52
11405752
Org Lett. 2008 Aug 7;10(15):3371-4
18588305
J Am Chem Soc. 2006 Dec 20;128(50):15960-1
17165709
Curr Med Chem Anticancer Agents. 2001 Aug;1(2):131-49
12678763
J Am Chem Soc. 2002 Nov 20;124(46):13644-5
12431072
Nat Prod Rep. 2004 Feb;21(1):77-93
15039836
Org Lett. 2000 Feb 24;2(4):461-4
10814351
Org Lett. 2004 Oct 14;6(21):3865-8
15469369
Org Lett. 2001 May 3;3(9):1363-6
11348235
J Org Chem. 2005 Sep 30;70(20):8035-46
16277325
J Antibiot (Tokyo). 1991 Nov;44(11):1259-61
1761423
Org Lett. 2005 Sep 15;7(19):4245-8
16146398
Chem Rev. 1999 May 12;99(5):1191-224
11749444
J Am Chem Soc. 2005 Aug 10;127(31):10818-9
16076173
Org Lett. 2005 Jun 9;7(12):2405-8
15932209
Tetrahedron. 2007 Jun 25;63(26):5768-5796
18575572