A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework.
Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole pi-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton.
Hong
Xuechuan
X
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
France
Stefan
S
Padwa
Albert
A
J Am Chem Soc. 2002 May 1;124(17):4628-41
11971711
Org Lett. 2001 May 31;3(11):1721-4
11405695
J Org Chem. 1998 Feb 6;63(3):556-565
11672045
J Org Chem. 1996 Nov 1;61(22):7882-7888
11667747
Angew Chem Int Ed Engl. 2002 Sep 2;41(17):3281-4
12207415
J Org Chem. 1997 Jan 10;62(1):78-87
11671366
Org Lett. 2004 Sep 16;6(19):3241-4
15355022
Org Lett. 2006 Oct 26;8(22):5141-4
17048863
J Org Chem. 2005 Mar 18;70(6):2206-18
15760207
Chem Rev. 1996 Feb 1;96(1):223-270
11848752
J Org Chem. 2000 May 5;65(9):2642-5
10808435
Org Lett. 2006 Jul 20;8(15):3275-8
16836384
J Org Chem. 2004 May 28;69(11):3735-45
15153003
J Am Chem Soc. 2002 Nov 6;124(44):13179-84
12405846
Org Lett. 2000 Jun 1;2(11):1625-7
10841495
Org Biomol Chem. 2005 Jan 21;3(2):213-5
15632959
J Org Chem. 2003 May 30;68(11):4195-205
12762718
J Org Chem. 2004 Dec 10;69(25):8796-803
15575760
Phytochemistry. 2004 Jul;65(14):2119-22
15279982
J Org Chem. 1997 Apr 4;62(7):2001-2010
11671503
J Am Chem Soc. 2002 Nov 13;124(45):13398-9
12418888
Org Lett. 2000 Nov 16;2(23):3599-601
11073654
Org Lett. 2005 Sep 29;7(20):4317-20
16178522
Chem Commun (Camb). 2004 Apr 7;(7):822-3
15045081
Org Lett. 2005 Sep 29;7(20):4539-42
16178578
J Org Chem. 1999 Jul 23;64(15):5670-5676
11674638