Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2011(20): 3301-3306
DOI: 10.1055/s-0030-1260203
DOI: 10.1055/s-0030-1260203
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkFormal Synthesis of Aspergillide A from Tri-O-acetyl-d-glucal
Further Information
Received
27 June 2011
Publication Date:
02 September 2011 (online)
Publication History
Publication Date:
02 September 2011 (online)

Abstract
We describe an efficient synthesis of a key intermediate in the synthesis of aspergillide A from a commercially available, chiral starting material.
Key words
Claisen rearrangement - allylic alcohol - stereoselective synthesis - tri-O-acetyl-d-glucal - aspergillide A
- 1
Kito K.Ookura R.Yoshida S.Namikoshi M.Ooi T.Kusumi T. Org. Lett. 2008, 10: 225 - 2
Nagasawa T.Kuwahara S. Org. Lett. 2009, 11: 761 - 3
Ookura R.Kito K.Saito Y.Kusumi T.Ooi T. Chem. Lett. 2009, 38: 384 - 4a
Sabitha G.Reddy DV.Rao AS.Yadav JS. Tetrahedron Lett. 2010, 51: 4195 - 4b
Fuwa H.Yamaguchi H.Sasaki M. Tetrahedron 2010, 66: 7492 - 4c
Fuwa H.Yamaguchi H.Sasaki M. Org. Lett. 2010, 12: 1848 - 4d
Diaz-Oltra S.Angulo-Pachon CA.Murga J.Carda M.Marco JA. J. Org. Chem. 2010, 75: 1775 - 4e
Nagasawa T.Kuwahara S. Tetrahedron Lett. 2010, 51: 875 - 4f
Kanematsu M.Yoshida M.Shishido K. Angew. Chem. Int. Ed. 2011, 50: 2618 - 4g
Izuchi Y.Kanomata N.Koshino H.Hongo Y.Nakata T.Takahashi S. Tetrahedron: Asymmetry 2011, 22: 246 - 4h
Nagasawa T.Nukada T.Kuwahara S. Tetrahedron 2011, 67: 2882 - 4i
Diaz-Oltra S.Angulo-Pachon CA.Murga J.Falomir E.Carda M.Marco JA. Chem. Eur. J. 2011, 17: 675 - 5a
Liu J.Xu K.He J.Zhang L.Pan X.She X. J. Org. Chem. 2009, 74: 5063 - 5b
Nagasawa T.Kuwahara S. Biosci., Biotechnol., Biochem. 2009, 73: 1893 - 5c
Diaz-Oltra S.Angulo-Pachon CA.Kneeteman MN.Murga J.Carda M.Marco JA. Tetrahedron Lett. 2009, 50: 3783 - 5d
Hande SM.Uenishi J. Tetrahedron Lett. 2009, 50: 189 - 5e
Mueller Hendrix AJ.Jennings MP. Tetrahedron Lett. 2010, 51: 4260 - 6a
Panarese JD.Waters SP. Org. Lett. 2009, 11: 5086 - 6b
Kanematsu M.Yoshida M.Shishido K. Tetrahedron Lett. 2011, 52: 1372 - 7
Gonzalo P.Pérez M.Gándara Z.Gómez G.Fall Y. Tetrahedron Lett. 2009, 50: 5285 - 8a
Mori Y.Hayashi H. J. Org. Chem. 2001, 66: 8666 - 8b
Hoberg JO. Carbohydr. Res. 1997, 300: 365 - 9a
Chen C.-L.Namba K.Kishi Y. Org. Lett. 2009, 11: 409 - 9b
Wallace GA.Scott RW.Heathcock CH. J. Org. Chem. 2000, 65: 4145 - 9c
Ireland RE.Wuts PGM.Ernst B. J. Am. Chem. Soc. 1981, 103: 3205 - For reviews related to the Claisen rearrangement in natural product synthesis, see:
- 9d
Trost BM.Brennan MK. Synthesis 2009, 3003 - 9e
Hewlett NM.Hupp CD.Tepe JJ. Synthesis 2009, 2825 - 9f
Rosenberg S.Leino R. Synthesis 2009, 2651 - 9g
Marcelli T.Hiemstra H. Synthesis 2010, 1229 - 9h
Dömling A.Huang Y. Synthesis 2010, 2859 - 10
Pérez-Sestelo J.Mascareñas JL.Castedo L.Mouriño A. J. Org. Chem. 1993, 58: 118 - 11
Yu M.Lynch V.Pagenkopf BL. Org. Lett. 2001, 3: 2563