Synthesis 2016; 48(05): 765-771
DOI: 10.1055/s-0035-1561114
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Decytospolide A, B and Their C-3 Epimers Using Stereoselective­ Oxypalladation

Yuji Kurogome
a   Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
,
Yasunao Hattori
b   Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan
,
Hidefumi Makabe*
a   Interdisciplinary Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan
c   Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano, 399-4598, Japan   Email: makabeh@shinshu-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 12 November 2015

Accepted after revision: 04 December 2015

Publication Date:
04 January 2016 (online)


Abstract

Stereoselective synthesis of decytospolide A and B and their C-3 epimers, which have a 2,6-cis-tetrahydropyran ring, has been achieved in high stereoselectivity and yield. The oxypalladation of single diastereomers of 6-(benzyloxy)-7-hydroxydodec-2-enyl 2-naphthoates was optimized to give products with a 2,6-cis-tetrahydropyran ring with high diastereoselectivity and yield.

Supporting Information

 
  • References


    • For recent reviews of the synthesis of tetrahydropyrans:
    • 1a Makabe H. Nat. Prod. Commun. 2013; 8: 1005
    • 1b Muzart J. J. Mol. Catal. A: Chem. 2010; 319: 1
    • 1c Muzart J. Tetrahedron 2005; 61: 5955
  • 2 Lu S, Sun P, Li T, Kurtán R, Mándi A, Antus S, Krohn H, Draeger S, Schulz B, Li Y, Li L, Zhang W. J. Org. Chem. 2011; 76: 9699
  • 3 Reddy PJ, Reddy AS, Yadav JS, Reddy BV. S. Tetrahedron Lett. 2012; 53: 4054
  • 4 Krishna PR, Nomula R, Ramana DV. Tetrahedron Lett. 2012; 53: 3612
  • 5 Zeng J, Tan YJ, Ma J, Leow ML, Tirtorahardjo D, Liu X.-W. Chem. Eur. J. 2014; 20: 405
  • 6 Clarisse D, Fache F. Tetrahedron Lett. 2014; 55: 2221
  • 7 Yahata K, Minami M, Watanabe K, Fujioka H. Org. Lett. 2014; 16: 3680
  • 8 Kammari BR, Bejjanki NK, Kommu N. Tetrahedron: Asymmetry 2015; 26: 296
  • 9 Srilatha M, Das B. Helv. Chim. Acta 2015; 98: 267
  • 10 Pazo M, Zuniga A, Perez M, Gomez G, Fall Y. Tetrahedron Lett. 2015; 56: 3774
    • 11a Hattori Y, Furuhata S, Okajima M, Konno H, Abe M, Miyoshi H, Goto T, Makabe H. Org. Lett. 2008; 10: 717
    • 11b Furuhata S, Hattori Y, Okajima M, Konno H, Abe M, Miyoshi H, Goto T, Makabe H. Tetrahedron 2008; 64: 7695
    • 12a Makabe H, Looi KK, Hirota M. Org. Lett. 2003; 5: 27
    • 12b Kurogome Y, Kogiso M, Looi KK, Hattori Y, Konno H, Hirota M, Makabe H. Tetrahedron 2013; 69: 8349
    • 12c Katsuyama M, Furuta M, Kobayashi K, Teruya K, Makabe H, Akaji K, Hattori Y. Heterocycles 2015; 91: 959
  • 13 Ohnishi K, Sakurai H, Kobayashi K, Makabe H, Teruya K, Akaji K, Hattori Y. Heterocycles 2015; 91: 573
  • 14 Dias LC, Ferreira MA. B. J. Org. Chem. 2012; 77: 4046
  • 15 Alam M, Wise C, Baxter CA, Cleator E, Walkinshaw A. Org. Process Res. Dev. 2012; 16: 435
  • 16 Aho JE, Piisola E, Krishnan KS, Pihko PM. Eur. J. Org. Chem. 2011; 1682
  • 17 Wang Y, Kang Q. Org. Lett. 2014; 16: 4190
  • 18 Ohtani I, Kusumi T, Kashman Y, Kakisawa H. J. Am. Chem. Soc. 1991; 113: 4092
  • 19 Krishna PR, Ramana DV. J. Org. Chem. 2012; 77: 674