Formal total synthesis of altohyrtin C (spongistatin 2). Part 1

Aldol approach to unite AB and CD spiroacetals

Takeshi Terauchi, Taro Terauchi, Ippei Sato, Wataru Shoji, Tomoharu Tsukada, Takashi Tsunoda, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.

Original languageEnglish
Pages (from-to)7741-7745
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number42
DOIs
Publication statusPublished - 2003 Oct 13

Fingerprint

Aldehydes
Carbon
Stereochemistry
altohyrtin C
alkoxyl radical
3-hydroxybutanal

Keywords

  • Aldol reaction
  • Altohyrtins
  • Spongistatins
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Terauchi, T., Terauchi, T., Sato, I., Shoji, W., Tsukada, T., Tsunoda, T., ... Nakata, M. (2003). Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals. Tetrahedron Letters, 44(42), 7741-7745. https://doi.org/10.1016/j.tetlet.2003.08.082

Formal total synthesis of altohyrtin C (spongistatin 2). Part 1 : Aldol approach to unite AB and CD spiroacetals. / Terauchi, Takeshi; Terauchi, Taro; Sato, Ippei; Shoji, Wataru; Tsukada, Tomoharu; Tsunoda, Takashi; Kanoh, Naoki; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 44, No. 42, 13.10.2003, p. 7741-7745.

Research output: Contribution to journalArticle

Terauchi, T, Terauchi, T, Sato, I, Shoji, W, Tsukada, T, Tsunoda, T, Kanoh, N & Nakata, M 2003, 'Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals', Tetrahedron Letters, vol. 44, no. 42, pp. 7741-7745. https://doi.org/10.1016/j.tetlet.2003.08.082
Terauchi, Takeshi ; Terauchi, Taro ; Sato, Ippei ; Shoji, Wataru ; Tsukada, Tomoharu ; Tsunoda, Takashi ; Kanoh, Naoki ; Nakata, Masaya. / Formal total synthesis of altohyrtin C (spongistatin 2). Part 1 : Aldol approach to unite AB and CD spiroacetals. In: Tetrahedron Letters. 2003 ; Vol. 44, No. 42. pp. 7741-7745.
@article{0346e5bb616f471eb0de37d8919c4c2d,
title = "Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals",
abstract = "The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.",
keywords = "Aldol reaction, Altohyrtins, Spongistatins, Stereoselective synthesis",
author = "Takeshi Terauchi and Taro Terauchi and Ippei Sato and Wataru Shoji and Tomoharu Tsukada and Takashi Tsunoda and Naoki Kanoh and Masaya Nakata",
year = "2003",
month = "10",
day = "13",
doi = "10.1016/j.tetlet.2003.08.082",
language = "English",
volume = "44",
pages = "7741--7745",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "42",

}

TY - JOUR

T1 - Formal total synthesis of altohyrtin C (spongistatin 2). Part 1

T2 - Aldol approach to unite AB and CD spiroacetals

AU - Terauchi, Takeshi

AU - Terauchi, Taro

AU - Sato, Ippei

AU - Shoji, Wataru

AU - Tsukada, Tomoharu

AU - Tsunoda, Takashi

AU - Kanoh, Naoki

AU - Nakata, Masaya

PY - 2003/10/13

Y1 - 2003/10/13

N2 - The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.

AB - The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.

KW - Aldol reaction

KW - Altohyrtins

KW - Spongistatins

KW - Stereoselective synthesis

UR - http://www.scopus.com/inward/record.url?scp=0141746177&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141746177&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2003.08.082

DO - 10.1016/j.tetlet.2003.08.082

M3 - Article

VL - 44

SP - 7741

EP - 7745

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 42

ER -