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

doi: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

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	7741-7745
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2003.08.082
Publication status	Published - 2003 Oct 13
Externally published	Yes

Keywords

Aldol reaction
Altohyrtins
Spongistatins
Stereoselective synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2003.08.082

Cite this

@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 = oct,

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

AN - SCOPUS:0141746177

SN - 0040-4039

VL - 44

SP - 7741

EP - 7745

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this