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Synlett 2005(2): 314-318
DOI: 10.1055/s-2004-837208
DOI: 10.1055/s-2004-837208
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of the Tetronate-Containing Core Structure of the Antibiotic Abyssomicin C
Weitere Informationen
Received
12 November 2004
Publikationsdatum:
17. Dezember 2004 (online)
Publikationsverlauf
Publikationsdatum:
17. Dezember 2004 (online)
Abstract
The core structure of abyssomicin C (1) containing an oxabicyclooctanone ring and a tetronate was prepared from the addition product of lithium ethyl propiolate and 4-tert-butyldimethylsilyloxycyclohexanone. Tetronate formation via addition of sodium methanolate followed by hydrolysis gave the hydroxy tetronic acid 27. The spiro compound 27 could be cyclized to the tricyclic tetronate 23 by a transannular Mitsunobu lactonization. Alternatively, 27 could be prepared from the cyanohydrin cis-19.
Key words
bicyclics - cyanohydrins - Mitsunobu - ring closure - Wittig reactions
- 1
Bister B.Bischoff D.Ströbele M.Riedlinger J.Reicke A.Bull AT.Zähner H.Fiedler H.-P.Süssmuth RD. Angew. Chem. 2004, 116: 2628 - 2
Riedlinger J.Reicke A.Zahner H.Krismer B.Bull AT.Maldonado LA.Ward AC.Goodfellow M.Bister B.Bischoff D.Süssmuth RD.Fiedler H.-P. J. Antibiotics 2004, 57: 271 - 3 See for example:
Nicolaou KC.Liu J.-J.Yang Z.Ueno H.Sorensen EJ.Claiborne CF.Guy RK.Hwang C.-K.Nakada M.Nantermet PG. J. Am. Chem. Soc. 1995, 117: 634 - For reviews, see:
-
4a
Yoshii E.Takeda K. Recent Prog. Chem. Synth. Antibiot. Relat. Microb. Prod. 1993, 67 -
4b
Tejedor D.Garcia-Tellado F. Org. Prep. Proced. Int. 2004, 36: 35 - 5
Bonjouklian R.Mynderse JS.Hunt AH.Deeter JB. Tetrahedron Lett. 1993, 34: 7857 - 6 For a summary of several tetronates, see:
Roush WR.Sciotti R. J. Am. Chem. Soc. 1998, 120: 7411 - For reviews, see:
-
7a
Ihara M.Fukumoto K. Angew. Chem., Int. Ed. Engl. 1993, 32: 1010 ; Angew. Chem. 1993, 105, 1059 -
7b
Tietze LF. Chem. Rev. 1996, 96: 115 - 8
Hagiwara H.Endou S.Fukushima M.Hoshi T.Suzuki T. Org. Lett. 2004, 6: 1115 ; and references therein - 9
Ley SV.Massi A. J. Chem. Soc., Perkin Trans. 1 2000, 3645 - 10
Terasawa T.Okada T. J. Org. Chem. 1977, 42: 1163 - 11
Lohrisch HJ.Kopanski L.Herrmann R.Schmidt H.Steglich W. Liebigs Ann. Chem. 1986, 177 -
12a
Ayres FD.Khan SI.Chapman OL.Kaganove SN. Tetrahedron Lett. 1994, 35: 7151 -
12b
Iwahama T.Yoshino Y.Keitoku T.Sakaguchi S.Ishii Y. J. Org. Chem. 2000, 65: 6502 -
12c
Kakiuchi N.Maeda Y.Nishimura T.Uemura S. J. Org. Chem. 2001, 66: 6620 - For alternative preparations of 18, see:
-
13a
Carreño MC.Urbano A.Di Vitta C. J. Org. Chem. 1998, 63: 8320 -
13b
Song ZL.Wang BM.Tu YQ.Fan CA.Zhang SY. Org. Lett. 2003, 5: 2319 - 14
Krepski LR.Lynch LE.Heilmann SM.Rasmussen JK. Tetrahedron Lett. 1985, 26: 981 -
15a
Buhler H.Bayer A.Effenberger F. Chem.-Eur. J. 2000, 6: 2564 -
15b
Effenberger F.Roos J.Kobler C.Buhler H. Can. J. Chem. 2002, 80: 671 - 16
Caine D.Smith TL. Synth. Commun. 1980, 10: 751 - 17 For a recent synthesis of a spirobicyclic tetronic acid by intramolecular Claisen condensation, see:
Page PCB.Vahedi H.Batchelor KJ.Hindley SJ.Edgar M.Beswick P. Synlett 2003, 1022 - For another method, see:
-
18a
Miyata O.Schmidt RR. Tetrahedron Lett. 1982, 23: 1793 -
18b
Hirsenkorn R.Schmidt RR. Liebigs Ann. Chem. 1990, 883 - 19 For a recent synthesis of spirocyclic butenolides by ring-closing metathesis, see:
Langer P.Albrecht U. Synlett 2002, 1841 -
20a
Evans DA.Carroll GL.Truesdale LK. J. Org. Chem. 1974, 39: 914 -
20b
Gassman PG.Talley JJ. Org. Synth. 1981, 60: 14 -
20c
Hünig S.Öller M. Chem. Ber. 1981, 114: 959 ; and references therein -
20d
Kim SS.Kim DW.Rajagopal G. Synthesis 2004, 213 - 21
Nagao Y.Goto M.Ochiai M. Chem. Lett. 1990, 1507 -
22a
Bestmann HJ.Schmidt M.Schobert R. Synthesis 1988, 49 -
22b
Bestmann HJ.Schobert R. Synthesis 1989, 419 - 23
Schobert R.Siegfried S.Gordon G.Nieuwenhuyzen M.Allenmark S. Eur. J. Org. Chem. 2001, 1951 - 24
Ruano JLG.Castro AMM.Rodriguez JH. J. Org. Chem. 1994, 59: 533 - 25 For the Mitsunobu reaction of tetronic acids, see:
Bajwa JS.Anderson RC. Tetrahedron Lett. 1990, 31: 6973 - 26 For the Mitsunobu reaction of α-hydroxy butenolides, see:
Langer P.Eckardt T.Stoll M. Org. Lett. 2000, 2: 2991 - 27 For related additions, see:
Knappwost-Gieseke C.Nerenz F.Wartchow R.Winterfeldt E. Chem.-Eur. J. 2004, 9: 3849 -
28a
Witiak DT.Tehim AK. J. Org. Chem. 1987, 52: 2324 -
28b
Takeda K.Yano S.Sato M.Yoshii E. J. Org. Chem. 1987, 52: 4135 - 29
Midland MM.Tramontano A.Cable JR. J. Org. Chem. 1980, 45: 28