Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion

Takeshi Terauchi, Masataka Morita, Kyoko Kimijima, Yasuhiro Nakamura, Gouichirou Hayashi, Taisaku Tanaka, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The C29-C44 portion of altohyrtins (spongistatins) has been prepared from 1,5-pentanediol and D-glucose in a stereoselective manner. The convergent synthesis relied on a coupling reaction of the C29-C37 vinyl bromide and the C38-C44 Weinreb amide, diastereoselective reduction of the C38 ketone, and stereoselective formation of the C33-C37 (E ring) acetal.

Original languageEnglish
Pages (from-to)5505-5508
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number32
DOIs
Publication statusPublished - 2001 Aug 6

Fingerprint

Acetals
Ketones
Amides
Glucose
1,5-pentanediol
vinyl bromide

Keywords

  • Altohyrtins
  • Spongistatins
  • Stereoselective synthesis
  • Weinreb coupling

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Terauchi, T., Morita, M., Kimijima, K., Nakamura, Y., Hayashi, G., Tanaka, T., ... Nakata, M. (2001). Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion. Tetrahedron Letters, 42(32), 5505-5508. https://doi.org/10.1016/S0040-4039(01)01069-3

Synthetic studies on altohyrtins (spongistatins) : Synthesis of the C29-C44 (EF) portion. / Terauchi, Takeshi; Morita, Masataka; Kimijima, Kyoko; Nakamura, Yasuhiro; Hayashi, Gouichirou; Tanaka, Taisaku; Kanoh, Naoki; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 42, No. 32, 06.08.2001, p. 5505-5508.

Research output: Contribution to journalArticle

Terauchi, T, Morita, M, Kimijima, K, Nakamura, Y, Hayashi, G, Tanaka, T, Kanoh, N & Nakata, M 2001, 'Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion', Tetrahedron Letters, vol. 42, no. 32, pp. 5505-5508. https://doi.org/10.1016/S0040-4039(01)01069-3
Terauchi T, Morita M, Kimijima K, Nakamura Y, Hayashi G, Tanaka T et al. Synthetic studies on altohyrtins (spongistatins): Synthesis of the C29-C44 (EF) portion. Tetrahedron Letters. 2001 Aug 6;42(32):5505-5508. https://doi.org/10.1016/S0040-4039(01)01069-3
Terauchi, Takeshi ; Morita, Masataka ; Kimijima, Kyoko ; Nakamura, Yasuhiro ; Hayashi, Gouichirou ; Tanaka, Taisaku ; Kanoh, Naoki ; Nakata, Masaya. / Synthetic studies on altohyrtins (spongistatins) : Synthesis of the C29-C44 (EF) portion. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 32. pp. 5505-5508.
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