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Synthesis 2017; 49(13): 2958-2970
DOI: 10.1055/s-0036-1588169
DOI: 10.1055/s-0036-1588169
paper
Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin
Weitere Informationen
Publikationsverlauf
Received: 26. Februar 2017
Accepted after revision: 13. März 2017
Publikationsdatum:
06. April 2017 (online)

Abstract
The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.
Key words
biselide A - haterumalides - macrolide - regioselective enzymatic hydrolysis - asymmetric aldol reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588169.
- Supporting Information
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References
- 1a Teruya T. Shimogawa H. Suenaga K. Kigoshi H. Chem. Lett. 2004; 33: 1184
- 1b Teruya T. Suenaga K. Maruyama S. Kurotaki M. Kigoshi H. Tetrahedron 2005; 61: 6561
- 2a Ueda K. Hu Y. Tetrahedron Lett. 1999; 40: 6305
- 2b Takada N. Sato H. Suenaga K. Arimoto H. Yamada K. Ueda K. Uemura D. Tetrahedron Lett. 1999; 40: 6309
- 3 Hoye TR. Wang J. J. Am. Chem. Soc. 2005; 127: 6950
- 4 Roulland E. Angew. Chem. Int. Ed. 2008; 47: 3762
- 5a Hayakawa I. Ueda M. Yamaura M. Ikeda Y. Suzuki Y. Yoshizato K. Kigoshi H. Org. Lett. 2008; 10: 1859
- 5b Ueda M. Yamaura M. Ikeda Y. Suzuki Y. Yoshizato K. Hayakawa I. Kigoshi H. J. Org. Chem. 2009; 74: 3370
- 5c Hayakawa I. Kigoshi H. J. Synth. Org. Jpn. 2010; 68: 814
- 6 Shomaker JM. Borhan B. J. Am. Chem. Soc. 2008; 130: 12228
- 7 Kigoshi H. Kita M. Ogawa S. Itoh M. Uemura D. Org. Lett. 2003; 5: 957
- 8a Synthesis of ent-haterumaralide NA methyl ester 6: Gu Y. Snider BB. Org. Lett. 2003; 5: 4385
- 8b Synthetic study of biselide E (8): Salit A.-F. Barbazanges M. Miege F. Larraufie M.-H. Meyer C. Cossy J. Synlett 2008; 2583
- 8c Synthetic study of haterumalides and biselides: Halperin SD. Kang B. Britton R. Synthesis 2011; 1946
- 8d Review: Kigoshi H. Hayakawa I. Chem. Rec. 2007; 7: 254
- 9a Satoh Y. Kawamura D. Yamaura M. Ikeda Y. Ochiai Y. Hayakawa I. Kigoshi H. Tetrahedron Lett. 2012; 53: 1390
- 9b Satoh Y. Yamada T. Onozaki Y. Kawamura D. Hayakawa I. Kigoshi H. Tetrahedron Lett. 2012; 53: 1393
- 10 Liron F. Fosse C. Pernolet A. Roulland E. J. Org. Chem. 2007; 72: 2220
- 11 In our previous synthesis of haterumalides,5 intermediate 9 was prepared by the following synthetic route (Scheme 8): four steps from olefin 34 to intermediate 9. In contrast, the synthetic route of Scheme 5 can provide 9 from 34 in two steps.
- 12 Lavallée C. Lemay G. Leborgne A. Spassky N. Prud’homme RE. Macromolecules 1984; 17: 2457
- 13 Dodier M. Quesnelle C. Marinier R. PCT Int. Appl WO 2008086128 A2, 2008
- 14 Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
- 15 Adam J.-M. Foricher J. Hanlon S. Lohri B. Moine G. Schmid R. Stahr H. Weber M. Wirz B. Zutter U. Org. Process Res. Dev. 2011; 15: 515
- 16 Hisano T. Onodera K. Toyabe Y. Mase N. Yoda H. Takabe K. Tetrahedron Lett. 2005; 46: 6293
- 17a Miura T. Kawashima Y. Umetsu S. Kanamori D. Tsuyama N. Jyo Y. Murakami Y. Imai N. Chem. Lett. 2007; 36: 814
- 17b Miura T. Umetsu S. Kanamori D. Tsuyama N. Jyo Y. Kawashima Y. Koyata N. Murakami Y. Imai N. Tetrahedron 2008; 64: 9305
- 18 Nagao Y. Hagiwara Y. Kumagai T. Ochiai M. Inoue T. Hashimoto K. Fujita E. J. Org. Chem. 1986; 51: 2391
- 19 Ohtani I. Kusumi T. Kashman Y. Kakisawa H. J. Am. Chem. Soc. 1991; 113: 4092
- 20 Inanaga J. Hirata K. Saeki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn. 1979; 52: 1989