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Synthesis 2010(3): 527-537
DOI: 10.1055/s-0029-1217145
DOI: 10.1055/s-0029-1217145
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of Halicholactone and Neohalicholactone
Further Information
Received
16 October 2009
Publication Date:
27 November 2009 (online)
Publication History
Publication Date:
27 November 2009 (online)
Abstract
New total syntheses of the marine oxylipins halicholactone and neohalicholactone are presented. The key building blocks were synthesized utilizing chemoenzymatic methods.
Key words
natural product - total synthesis - enzymes - boron reagents - asymmetric synthesis
-
1a
Cragg GM.Grothaus PG.Newman DJ. Chem. Rev. 2009, 109: 3012 -
1b
Blunt JW.Copp BR.Hu W.-P.Munro MHG.Northcote PT.Prinsep MR. Nat. Prod. Rep. 2009, 26: 170 -
1c
Li M.-Y.Xiao Q.Pan J.-Y.Wu J. Nat. Prod. Rep. 2009, 26: 281 - 2
White JD.Yang J. Synlett 2009, 1713 - Synthesis of constanolactones A + B:
-
3a
Pietruszka J.Wilhelm T. Synlett 2003, 1698 - Enzymatic approaches:
-
3b
Pietruszka J.Rieche ACM.Wilhelm T.Witt A. Adv. Synth. Catal. 2003, 345: 1273 -
3c
Fischer T.Pietruszka J. Adv. Synth. Catal. 2007, 349: 1533 - Synthesis of constanolactones C + D:
-
4a
Pietruszka J.Rieche ACM.Schöne N. Synlett 2007, 2525 - Synthesis of solandelactones A-H:
-
4b
Pietruszka J.Rieche ACM. Adv. Synth. Catal. 2008, 350: 1407 - Boron reagents:
-
4c
Pietruszka J.Schöne N. Angew. Chem. Intl. Ed. 2003, 42: 5638 -
4d
Pietruszka J.Schöne N. Eur. J. Org. Chem. 2004, 5011 -
4e
Pietruszka J.Schöne N. Synthesis 2006, 24 -
4f
Pietruszka J.Schöne N.Frey W.Grundl L. Chem. Eur. J. 2008, 14: 5178 -
4g
Fernandez E.Pietruszka J. Synlett 2009, 1474 - Isolation:
-
5a
Nagle DG.Gerwick WH. Tetrahedron Lett. 1990, 31: 2995 -
5b
Nagle DG.Gerwick WH. J. Org. Chem. 1994, 59: 7227 - Completed total syntheses:
-
5c
White JD.Jensen MS. J. Am. Chem. Soc. 1995, 117: 6224 -
5d
Barloy-Da Silva C.Benkouider A.Pale P. Tetrahedron Lett. 2000, 41: 3077 -
5e
Yu J.Lai J.-Y.Ye J.Balu N.Reddy LM.Duan W.Fogel ER.Capdevila JH.Falck JR. Tetrahedron Lett. 2002, 43: 3939 -
5f
Miyaoka H.Shigemoto T.Yamada Y. Heterocycles 1998, 47: 415 -
5g
Miyaoka H.Shigemoto T.Tamura M.Yamada Y. Heterocycles 1998, 40: 205 -
5h
Miyaoka H.Shigemoto T.Yamada Y. Tetrahedron Lett. 1996, 37: 7407 -
5i
See also references 3a and 4a.
- Isolation:
-
6a
Seo Y.Cho KW.Rho J.-R.Shin J. Tetrahedron 1996, 52: 10583 - Completed total syntheses (A, B, E, and F):
-
6b
Davoren JE.Martin SF. J. Am. Chem. Soc. 2007, 129: 510 -
6c
White JD.Martin WHC.Lincoln C.Yang J. Org. Lett. 2007, 9: 3481 -
6d
Davoren JE.Harcken C.Martin SF. J. Org. Chem. 2008, 73: 391 -
6e
White JD.Lincoln CM.Yang J.Martin WHC.Chan DB. J. Org. Chem. 2008, 73: 4139 -
6f
See also reference 4b.
-
7a
Niwa H.Wakamatsu K.Yamada K. Tetrahedron Lett. 1989, 30: 4543 -
7b
Kigoshi H.Niwa H.Yamada K.Stout TJ.Clardy J. Tetrahedron Lett. 1991, 32: 2427 - 8
Proteau PJ.Rossi JV.Gerwick WH. J. Nat. Prod. 1994, 57: 1717 -
9a
Critcher DJ.Connolly S.Wills M. Tetrahedron Lett. 1995, 36: 3763 -
9b
Critcher DJ.Connolly S.Mahon MF.Wills M. Chem. Commun. 1995, 139 -
9c
Critcher DJ.Connolly S.Wills M. J. Org. Chem. 1997, 62: 6638 -
10a
Takemoto Y.Baba Y.Saha G.Nakao S.Iwata C.Tanaka T.Ibuka T. Tetrahedron Lett. 2000, 41: 3653 -
10b
Baba Y.Saha G.Nakao S.Iwata C.Tanaka T.Ibuka T.Ohishi H.Takemoto Y. J. Org. Chem. 2001, 66: 81 - 11
Takahashi T.Watanabe H.Kitahara T. Heterocycles 2002, 58: 99 - 12
Zhu C.-Y.Cao X.-Y.Zhu B.-H.Deng C.Sun X.-L.Wang B.-Q.Shen Q.Tang Y. Chem. Eur. J. 2009, 15: 11465 -
13a
Chen C.Tagami K.Kishi Y. J. Org. Chem. 1995, 60: 5386 -
13b
Kishi Y. Tetrahedron 2002, 58: 6239 - 14 For example:
Schmidt M.Hasenpusch D.Kähler M.Kirchner U.Wiggenhorn K.Langel W.Bornscheuer UT. ChemBioChem 2006, 805 ; and references cited therein - 15 Review:
Müller M.Wolberg M.Schubert T.Hummel W. Adv. Biochem. Eng. Biotechnol. 2005, 92: 261 ; and references cited therein -
16a
Schubert T.Hummel W.Kula M.-R.Müller M. Eur. J. Org. Chem. 2001, 4181 -
16b
Heiss C.Phillips RS. J. Chem. Soc., Perkin Trans. 1 2000, 2821 -
18a
Denmark SE.Jones TK. J. Org. Chem. 1982, 47: 4595 -
18b
Harris NJ.Gajewski JJ. J. Am. Chem. Soc. 1994, 116: 6121 -
18c
Plater MJ.Aiken S.Bourhill G. Tetrahedron 2002, 58: 2415 - 19
Bischop M.Cmrecki V.Ophoven V.Pietruszka J. Synthesis 2008, 2488 - 20
Zhang D.Ready JM. J. Am. Chem. Soc. 2007, 129: 12088 -
21a
Dess DB.Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 -
21b
Wavrin L.Viala J. Synthesis 2002, 326 - 22
Kubota K.Leighton JL. Angew. Chem. Int. Ed. 2003, 42: 946 -
23a
Fürstner A.Guth O.Düffels A.Seidel G.Liebl M.Gabor B.Mynott R. Chem. Eur. J. 2001, 7: 4811 -
23b
Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 - 24
Sasaki H.Boyall D.Carreira EM. Helv. Chim. Acta 2001, 84: 964 - 25
Prakesch M.Gree D.Gree R. J. Org. Chem. 2001, 66: 3146 - 26
Suzuki M.Kiho T.Tomokiyo K.Furuta K.Fukushima S.Takeuchi Y.Nakanishi M.Noyori R. J. Med. Chem. 1998, 41: 3084 - 27
Luo F.-T.Negishi E.-i. J. Org. Chem. 1985, 50: 4762 - 28
Kluge AF.Untch KG.Fried JH. J. Am. Chem. Soc. 1972, 94: 7827 - 29
Bernady KF.Floyd MB.Poletto JF.Weiss MJ. J. Org. Chem. 1979, 44: 1438 - 30
Sha W.Salomon RG. J. Org. Chem. 2000, 65: 5315 - 31
Yadav JS.Deshpande PK.Sharma GVM. Tetrahedron 1992, 48: 4465
References
All enzymes are commercially available from Codexis Inc. and were used as purchased.