Synthesis, Inhaltsverzeichnis FEATUREARTICLE© Georg Thieme Verlag Stuttgart ˙ New YorkTotal Synthesis of Halicholactone and NeohalicholactoneMartina Bischop, Verena Doum, Anja C. M. Nordschild née Rieche, Jörg Pietruszka*, Diana SandkuhlInstitut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, Stetternicher Forst Geb. 15.8, 52426 Jülich, GermanyFax: +49(2461)616196; e-Mail: j.pietruszka@fz-juelich.de; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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 Volltext Referenzen References <A NAME="RE25809SS-1A">1a</A> Cragg GM. Grothaus PG. Newman DJ. Chem. Rev. 2009, 109: 3012 <A NAME="RE25809SS-1B">1b</A> Blunt JW. Copp BR. Hu W.-P. Munro MHG. Northcote PT. Prinsep MR. Nat. Prod. Rep. 2009, 26: 170 <A NAME="RE25809SS-1C">1c</A> Li M.-Y. Xiao Q. Pan J.-Y. Wu J. Nat. Prod. Rep. 2009, 26: 281 <A NAME="RE25809SS-2">2</A> White JD. Yang J. Synlett 2009, 1713 Synthesis of constanolactones A + B: <A NAME="RE25809SS-3A">3a</A> Pietruszka J. Wilhelm T. Synlett 2003, 1698 Enzymatic approaches: <A NAME="RE25809SS-3B">3b</A> Pietruszka J. Rieche ACM. Wilhelm T. Witt A. Adv. Synth. Catal. 2003, 345: 1273 <A NAME="RE25809SS-3C">3c</A> Fischer T. Pietruszka J. Adv. Synth. Catal. 2007, 349: 1533 Synthesis of constanolactones C + D: <A NAME="RE25809SS-4A">4a</A> Pietruszka J. Rieche ACM. Schöne N. Synlett 2007, 2525 Synthesis of solandelactones A-H: <A NAME="RE25809SS-4B">4b</A> Pietruszka J. Rieche ACM. Adv. Synth. Catal. 2008, 350: 1407 Boron reagents: <A NAME="RE25809SS-4C">4c</A> Pietruszka J. Schöne N. Angew. Chem. Intl. Ed. 2003, 42: 5638 <A NAME="RE25809SS-4D">4d</A> Pietruszka J. Schöne N. Eur. J. Org. Chem. 2004, 5011 <A NAME="RE25809SS-4E">4e</A> Pietruszka J. Schöne N. Synthesis 2006, 24 <A NAME="RE25809SS-4F">4f</A> Pietruszka J. Schöne N. Frey W. Grundl L. Chem. Eur. J. 2008, 14: 5178 <A NAME="RE25809SS-4G">4g</A> Fernandez E. Pietruszka J. Synlett 2009, 1474 Isolation: <A NAME="RE25809SS-5A">5a</A> Nagle DG. Gerwick WH. Tetrahedron Lett. 1990, 31: 2995 <A NAME="RE25809SS-5B">5b</A> Nagle DG. Gerwick WH. J. Org. Chem. 1994, 59: 7227 Completed total syntheses: <A NAME="RE25809SS-5C">5c</A> White JD. Jensen MS. J. Am. Chem. Soc. 1995, 117: 6224 <A NAME="RE25809SS-5D">5d</A> Barloy-Da Silva C. Benkouider A. Pale P. Tetrahedron Lett. 2000, 41: 3077 <A NAME="RE25809SS-5E">5e</A> Yu J. Lai J.-Y. Ye J. Balu N. Reddy LM. Duan W. Fogel ER. Capdevila JH. Falck JR. Tetrahedron Lett. 2002, 43: 3939 <A NAME="RE25809SS-5F">5f</A> Miyaoka H. Shigemoto T. Yamada Y. Heterocycles 1998, 47: 415 <A NAME="RE25809SS-5G">5g</A> Miyaoka H. Shigemoto T. Tamura M. Yamada Y. Heterocycles 1998, 40: 205 <A NAME="RE25809SS-5H">5h</A> Miyaoka H. Shigemoto T. Yamada Y. Tetrahedron Lett. 1996, 37: 7407 <A NAME="RE25809SS-5I">5i</A> See also references 3a and 4a. Isolation: <A NAME="RE25809SS-6A">6a</A> Seo Y. Cho KW. Rho J.-R. Shin J. Tetrahedron 1996, 52: 10583 Completed total syntheses (A, B, E, and F): <A NAME="RE25809SS-6B">6b</A> Davoren JE. Martin SF. J. Am. Chem. Soc. 2007, 129: 510 <A NAME="RE25809SS-6C">6c</A> White JD. Martin WHC. Lincoln C. Yang J. Org. Lett. 2007, 9: 3481 <A NAME="RE25809SS-6D">6d</A> Davoren JE. Harcken C. Martin SF. J. Org. Chem. 2008, 73: 391 <A NAME="RE25809SS-6E">6e</A> White JD. Lincoln CM. Yang J. Martin WHC. Chan DB. J. Org. Chem. 2008, 73: 4139 <A NAME="RE25809SS-6F">6f</A> See also reference 4b. <A NAME="RE25809SS-7A">7a</A> Niwa H. Wakamatsu K. Yamada K. Tetrahedron Lett. 1989, 30: 4543 <A NAME="RE25809SS-7B">7b</A> Kigoshi H. Niwa H. Yamada K. Stout TJ. Clardy J. Tetrahedron Lett. 1991, 32: 2427 <A NAME="RE25809SS-8">8</A> Proteau PJ. Rossi JV. Gerwick WH. J. Nat. Prod. 1994, 57: 1717 <A NAME="RE25809SS-9A">9a</A> Critcher DJ. Connolly S. Wills M. Tetrahedron Lett. 1995, 36: 3763 <A NAME="RE25809SS-9B">9b</A> Critcher DJ. Connolly S. Mahon MF. Wills M. Chem. Commun. 1995, 139 <A NAME="RE25809SS-9C">9c</A> Critcher DJ. Connolly S. Wills M. J. Org. Chem. 1997, 62: 6638 <A NAME="RE25809SS-10A">10a</A> Takemoto Y. Baba Y. Saha G. Nakao S. Iwata C. Tanaka T. Ibuka T. Tetrahedron Lett. 2000, 41: 3653 <A NAME="RE25809SS-10B">10b</A> Baba Y. Saha G. Nakao S. Iwata C. Tanaka T. Ibuka T. Ohishi H. Takemoto Y. J. Org. Chem. 2001, 66: 81 <A NAME="RE25809SS-11">11</A> Takahashi T. Watanabe H. Kitahara T. Heterocycles 2002, 58: 99 <A NAME="RE25809SS-12">12</A> 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 <A NAME="RE25809SS-13A">13a</A> Chen C. Tagami K. Kishi Y. J. Org. Chem. 1995, 60: 5386 <A NAME="RE25809SS-13B">13b</A> Kishi Y. Tetrahedron 2002, 58: 6239 <A NAME="RE25809SS-14">14</A> For example: Schmidt M. Hasenpusch D. Kähler M. Kirchner U. Wiggenhorn K. Langel W. Bornscheuer UT. ChemBioChem 2006, 805 ; and references cited therein <A NAME="RE25809SS-15">15</A> Review: Müller M. Wolberg M. Schubert T. Hummel W. Adv. Biochem. Eng. Biotechnol. 2005, 92: 261 ; and references cited therein <A NAME="RE25809SS-16A">16a</A> Schubert T. Hummel W. Kula M.-R. Müller M. Eur. J. Org. Chem. 2001, 4181 <A NAME="RE25809SS-16B">16b</A> Heiss C. Phillips RS. J. Chem. Soc., Perkin Trans. 1 2000, 2821 <A NAME="RE25809SS-17">17</A> All enzymes are commercially available from Codexis Inc. and were used as purchased. <A NAME="RE25809SS-18A">18a</A> Denmark SE. Jones TK. J. Org. Chem. 1982, 47: 4595 <A NAME="RE25809SS-18B">18b</A> Harris NJ. Gajewski JJ. J. Am. Chem. Soc. 1994, 116: 6121 <A NAME="RE25809SS-18C">18c</A> Plater MJ. Aiken S. Bourhill G. Tetrahedron 2002, 58: 2415 <A NAME="RE25809SS-19">19</A> Bischop M. Cmrecki V. Ophoven V. Pietruszka J. Synthesis 2008, 2488 <A NAME="RE25809SS-20">20</A> Zhang D. Ready JM. J. Am. Chem. Soc. 2007, 129: 12088 <A NAME="RE25809SS-21A">21a</A> Dess DB. Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 <A NAME="RE25809SS-21B">21b</A> Wavrin L. Viala J. Synthesis 2002, 326 <A NAME="RE25809SS-22">22</A> Kubota K. Leighton JL. Angew. Chem. Int. Ed. 2003, 42: 946 <A NAME="RE25809SS-23A">23a</A> Fürstner A. Guth O. Düffels A. Seidel G. Liebl M. Gabor B. Mynott R. Chem. Eur. J. 2001, 7: 4811 <A NAME="RE25809SS-23B">23b</A> Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 <A NAME="RE25809SS-24">24</A> Sasaki H. Boyall D. Carreira EM. Helv. Chim. Acta 2001, 84: 964 <A NAME="RE25809SS-25">25</A> Prakesch M. Gree D. Gree R. J. Org. Chem. 2001, 66: 3146 <A NAME="RE25809SS-26">26</A> Suzuki M. Kiho T. Tomokiyo K. Furuta K. Fukushima S. Takeuchi Y. Nakanishi M. Noyori R. J. Med. Chem. 1998, 41: 3084 <A NAME="RE25809SS-27">27</A> Luo F.-T. Negishi E.-i. J. Org. Chem. 1985, 50: 4762 <A NAME="RE25809SS-28">28</A> Kluge AF. Untch KG. Fried JH. J. Am. Chem. Soc. 1972, 94: 7827 <A NAME="RE25809SS-29">29</A> Bernady KF. Floyd MB. Poletto JF. Weiss MJ. J. Org. Chem. 1979, 44: 1438 <A NAME="RE25809SS-30">30</A> Sha W. Salomon RG. J. Org. Chem. 2000, 65: 5315 <A NAME="RE25809SS-31">31</A> Yadav JS. Deshpande PK. Sharma GVM. Tetrahedron 1992, 48: 4465
