Abstract
The unique tricarbocyclic system in GKK1032A2 , an antitumor agent from Penicillium sp. GKK1032, was constructed in a highly stereoselective manner, starting from a
readily available Hajos-Wiechert ketone analog.
Key words
antitumor agents - carbocycles - Diels-Alder reactions - natural products - stereoselective
synthesis
References
1a </A>
Koizumi F,
Hasegawa A,
Ando K,
Ogawa T, and
Hara M. inventors; Jpn. Kokai Tokkyo Koho, JP 2001247574 A2 20010911.
; Chem. Abstr. 2001 , 135 , 209979
1b </A>
Hasegawa A.
Koizumi F.
Takahashi Y.
Ando K.
Ogawa T.
Hara M.
Yoshida M.
43rd Symposium on the Chemistry of Natural Products, Symposium Papers
Osaka;
Japan:
2001.
p.467
<A NAME="RU10005ST-2">2 </A>
Omura S,
Komiyama H,
Hayashi M,
Masuma R, and
Fukaumi A. inventors; Jpn. Kokai Tokkyo Koho, JP 2002255969 A2 20020911.
; Chem. Abstr. 2002 , 137 , 231476
<A NAME="RU10005ST-3">3 </A>
He HY.
Yang HY.
Bigelis R.
Solum EH.
Greenstein M.
Carter GT.
Tetrahedron Lett.
2002,
43:
1633
<A NAME="RU10005ST-4">4 </A>
Oikawa H.
J. Org. Chem.
2003,
68:
3552
<A NAME="RU10005ST-5">5 </A>
Hagiwara H.
Sakai H.
Uchiyama T.
Ito Y.
Morita N.
Hoshi T.
Suzuki T.
Ando M.
J. Chem. Soc., Perkin Trans. 1
2002,
583
<A NAME="RU10005ST-6">6 </A>
McKenzie TC.
J. Org. Chem.
1974,
39:
629
<A NAME="RU10005ST-7">7 </A>
Renoud-Grappin M.
Vanucci C.
Lhommet G.
J. Org. Chem.
1994,
59:
3902
<A NAME="RU10005ST-8">8 </A>
Hajos ZG.
Parrish DR.
J. Org. Chem.
1973,
38:
3239
9a </A>
Provita J.
Ocadlik R.
Klinotova E.
Klinot J.
Vystrcil A.
Collect. Czech. Chem. Commun.
1987,
52:
501
9b </A>
Kawabata T.
Grieco PA.
Sham H.-L.
Kim H.
Jaw JY.
Tu S.
J. Org. Chem.
1987,
52:
3346
9c </A>
Mehta G.
Murthy AN.
J. Org. Chem.
1987,
52:
2875
9d </A>
Ihara M.
Tokunaga Y.
Fukumoto K.
J. Org. Chem.
1990,
55:
4497
<A NAME="RU10005ST-10">10 </A>
Mancuso AJ.
Swern D.
Synthesis
1981,
165
11a </A>
Minami I.
Takahashi K.
Shimizu I.
Kimura T.
Tsuji J.
Tetrahedron
1986,
42:
2971
11b </A>
Ito Y.
Hirao T.
Saegusa T.
J. Org. Chem.
1978,
43:
1011
<A NAME="RU10005ST-12">12 </A>
Krafft ME.
Dasse OA.
Fu Z.
J. Org. Chem.
1999,
64:
2475
13a </A>
Nicholls B.
Whiting MC.
J. Chem. Soc.
1959,
551
13b </A>
Ghavshou M.
Widdowson DA.
J. Chem. Soc., Perkin Trans. 1
1983,
3065
<A NAME="RU10005ST-14">14 </A>
Tanaka T.
Mikamiyama H.
Maeda K.
Ishida T.
In Y.
Iwata C.
Chem. Commun.
1997,
2401
15a </A>
Corey EJ.
Erickson BW.
J. Org. Chem.
1971,
36:
3553
15b </A>
Ho T.-L.
Wong CM.
Can. J. Chem.
1972,
50:
3740
15c </A>
Ho T.-L.
Ho CH.
Wong CM.
J. Chem. Soc., Chem. Commun.
1972,
791
15d </A>
Fetizon M.
Jurion M.
J. Chem. Soc., Chem. Commun.
1972,
382
<A NAME="RU10005ST-16">16 </A>
Stork G.
Zhao K.
Tetrahedron Lett.
1989,
30:
287
<A NAME="RU10005ST-17">17 </A>
Langille NF.
Dakin LA.
Panek JS.
Org. Lett.
2003,
5:
575
<A NAME="RU10005ST-18">18 </A>
Posner GH.
Org. React.
1972,
19:
1
<A NAME="RU10005ST-19">19 </A>
Horiguchi Y.
Nakamura E.
Kuwajima I.
Org. Synth., Coll. Vol. IX
Wiley and Sons;
New York:
1998.
p.564
<A NAME="RU10005ST-20">20 </A>
Sakata H.
Aoki Y.
Kuwajima I.
Tetrahedron Lett.
1990,
31:
1161
<A NAME="RU10005ST-21">21 </A>
Corey EJ.
Hopkins PB.
Tetrahedron Lett.
1982,
23:
4871
22a </A>
Torneiro M.
Fall Y.
Castedo L.
Mourino A.
Tetrahedron Lett.
1992,
33:
105
22b </A>
Denmark SE.
Fujimori S.
Org. Lett.
2002,
4:
3473
<A NAME="RU10005ST-23">23 </A>
Comins DL.
Dehghani A.
Tetrahedron Lett.
1992,
33:
6299
<A NAME="RU10005ST-24">24 </A>
Marshall JA.
Van Devender EA.
J. Org. Chem.
2001,
66:
8037
<A NAME="RU10005ST-25">25 </A>
Crystallographic data for 22 : formula, C37 H60 O2 Si; FW, 612.94; crystal system, orthorhombic; space group, P 21 21 21 ; a = 11.7726 (4) Å, b = 12.9543 (4) Å, c = 23.5023 (8) Å; V = 3584.2 (2) Å3 ; Z = 4; T = 170 K; D
calcd = 1.136 g cm-1 ; λ(MoK
α ) = 0.71070 Å; R 1 = 0.0418 [I>2σ(Ι )]; wR 2 = 0.1082; GOF(F
2 ) = 1.064.
26a </A>
Danishefsky S.
Schuda PF.
Kitahara T.
Etheredge SJ.
J. Am. Chem. Soc.
1977,
99:
6066
26b </A>
Stevens RV.
Albizati KF.
J. Org. Chem.
1985,
50:
632
