Abstract
An efficient total synthesis of (+)-bongkrekic acid,
a potent apoptosis inhibitor, has been accomplished by employing
a convergent strategy based on the Suzuki-Miyaura coupling
of three fully functionalized segments.
Key words
apoptosis - conjugated diene - Suzuki-Miyaura
coupling - palladium - bongkrekic acid
References
<A NAME="RC03009SS-1A">1a </A>
van Veen AG.
Mertens WK.
Recl. Trav. Chim. Pays-Bas
1934,
53:
257
<A NAME="RC03009SS-1B">1b </A>
Lijimbach GWM.
Cox HC.
Berends W.
Tetrahedron
1970,
26:
5993
<A NAME="RC03009SS-1C">1c </A>
Lijimbach GWM.
Cox HC.
Berends W.
Tetrahedron
1971,
27:
1839
<A NAME="RC03009SS-1D">1d </A>
De Bruijin J.
Frost DJ.
Nugteren DH.
Gaudemer A.
Lijimbach GWM.
Cox HC.
Brends W.
Tetrahedron
1973,
29:
1541
<A NAME="RC03009SS-1E">1e </A>
Zyblir J.
Gaudemer F.
Gaudemer A.
Experientia
1973,
29:
648
<A NAME="RC03009SS-2">2 </A>
Stubb M.
Pharmacol.
Ther.
1979,
7:
329
<A NAME="RC03009SS-3A">3a </A>
Marchetti P.
Castedo M.
Susin SA.
Zamzami N.
Hirsch T.
Macho A.
Haeffner A.
Hirsh T.
Geuskens M.
Kroemer G.
J. Exp.
Med.
1996,
184:
1155
<A NAME="RC03009SS-3B">3b </A>
Marchetti P.
Hirsh T.
Zamzami N.
Castedo M.
Decaudin D.
Susin SA.
Masse B.
Kroemer G.
J. Immunol.
1996,
157:
4830
<A NAME="RC03009SS-4">4 </A>
Corey EJ.
Tramontano J.
J. Am. Chem. Soc.
1984,
106:
462
<A NAME="RC03009SS-5">5 </A>
Shindo M.
Sugioka T.
Umaba Y.
Shishido K.
Tetrahedron Lett.
2004,
45:
8863
<A NAME="RC03009SS-6A">6a </A>
Miyaura N.
Suzuki A.
Chem.
Rev.
1995,
95:
2457
<A NAME="RC03009SS-6B">6b </A>
Suzuki A.
Brown HC.
Organic
Synthesis via Boranes: Suzuki Coupling
Vol.
3:
Aldrich Chemical Company, Inc.;
Milwaukee:
2003.
<A NAME="RC03009SS-7">7 </A>
It has been clarified that the C1-MOM
ester can be hydrolyzed under acidic conditions without any isomerization
of the 2,4-diene moiety in our laboratories.
<A NAME="RC03009SS-8">8 </A>
Corey EJ.
Katzenellenbogen JA.
Posner GH.
J. Am. Chem. Soc.
1967,
89:
4245
<A NAME="RC03009SS-9">9 </A> Addition of 0.1 equiv t -BuOK gave better yields (79%)
than without it (61-69%), see:
Abe T.
Higa T.
Negi S.
Morita Y.
Takayanagi K.
Hamamura K.
Tetrahedron
2000,
57:
2701
<A NAME="RC03009SS-10">10 </A>
Bal BS.
Childers WE.
Pinnick HW.
Tetrahedron
1981,
37:
2091
<A NAME="RC03009SS-11">11 </A>
Evans DA.
Ennis MD.
Mathre DJ.
J. Am. Chem. Soc.
1982,
104:
1737
<A NAME="RC03009SS-12">12 </A>
Crimmins MT.
Debaillie AC.
J. Am. Chem. Soc.
2006,
128:
4936
<A NAME="RC03009SS-13">13 </A>
Johnson WS.
Werthemann L.
Bartlett WR.
Brocksom TJ.
Li T.-T.
Faulkner DJ.
Peterson MR.
J. Am. Chem. Soc.
1970,
92:
741
<A NAME="RC03009SS-14">14 </A>
Avedissian H.
Sinha SC.
Yazbak A.
Sinha A.
Neogi P.
Sinha SC.
Keinan E.
J.
Org. Chem.
2000,
65:
6035
<A NAME="RC03009SS-15A">15a </A>
Takai K.
Shinomiya N.
Kaihara H.
Yoshida N.
Moriwake T.
Utimoto K.
Synlett
1995,
963
<A NAME="RC03009SS-15B">15b </A>
Takai K.
Hikasa T.
Ichiguchi T.
Sumino N.
Synlett
1999,
1769
<A NAME="RC03009SS-15C">15c </A>
Takai K.
Kunisada Y.
Tachibana Y.
Yamaji N.
Nakatani E.
Bull.
Chem. Soc. Jpn.
2004,
77:
1581
<A NAME="RC03009SS-16">16 </A>
Matsuura F.
Peters R.
Anada M.
Harried SS.
Hao J.
Kishi Y.
J. Am. Chem. Soc.
2006,
128:
7463
<A NAME="RC03009SS-17">17 </A>
Hartung IV.
Niess B.
Haustedt LO.
Hoffmann HMR.
Org. Lett.
2002,
4:
3239
<A NAME="RC03009SS-18">18 </A>
Corey EJ.
Fuchs PL.
Tetrahedron Lett.
1972,
13:
3769
<A NAME="RC03009SS-19">19 </A>
Corey EJ.
Katzenellenbogen JA.
J. Am. Chem.
Soc.
1969,
91:
1851
<A NAME="RC03009SS-20">20 </A>
Guindon Y.
Murtagh L.
Caron V.
Landry SR.
Jung G.
Bencheqroum M.
Faucher A.-M.
Guérin B.
J. Org. Chem.
2001,
66:
5427
<A NAME="RC03009SS-21A">21a </A>
Stork G.
Zhao K.
Tetrahedron
Lett.
1989,
30:
2173
<A NAME="RC03009SS-21B">21b </A>
Seyferth D.
Heerex JK.
Sixgh G.
Grim SO.
Hughes WB.
J.
Organomet. Chem.
1966,
5:
267
<A NAME="RC03009SS-22">22 </A>
Viguier RFH.
Hulme AN.
J.
Am. Chem. Soc.
2006,
128:
11370
<A NAME="RC03009SS-23">23 </A>
Shibuya M.
Tomizawa M.
Suzuki I.
Iwabuchi Y.
J. Am. Chem. Soc.
2006,
128:
8412
<A NAME="RC03009SS-24">24 </A>
Since the optical rotation of the
trimethyl ester derived from our synthetic BA was identical to that
of the trimethyl ester derived from the natural BA, it was revealed
that the optical rotation reported by Berends¹b was
incorrect.
<A NAME="RC03009SS-25">25 </A>
Data for the trimethyl ester derived
from the natural BA.