Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments

Takeshi Terauchi; Taisaku Tanaka; Taro Terauchi; Masataka Morita; Kyoko Kimijima; Ippei Sato; Wataru Shoji; Yasuhiro Nakamura; Tomoharu Tsukada; Takashi Tsunoda; Gouichirou Hayashi; Naoki Kanoh; Masaya Nakata

doi:10.1016/j.tetlet.2003.08.083

Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments

Takeshi Terauchi, Taisaku Tanaka, Taro Terauchi, Masataka Morita, Kyoko Kimijima, Ippei Sato, Wataru Shoji, Yasuhiro Nakamura, Tomoharu Tsukada, Takashi Tsunoda, Gouichirou Hayashi, Naoki Kanoh, Masaya Nakata

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

27 Citations (Scopus)

Abstract

Coupling of the C1-C14 (AB) crotylstannane with the C15-C28 (CD) aldehyde followed by stereochemical arrangements gave the C1-C28 (ABCD) fragment of altohyrtin C. The C29-C44 (EF) fragment was also prepared. The syntheses of these two fragments, both of which were identical with those prepared by the Smith group, constitute a formal total synthesis of altohyrtin C.

Original language	English
Pages (from-to)	7747-7751
Number of pages	5
Journal	Tetrahedron Letters
Volume	44
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2003.08.083
Publication status	Published - 2003 Oct 13
Externally published	Yes

Keywords

Altohyrtins
Crotylstannanes
Spongistatins
Stereoselective synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2003.08.083

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Terauchi, T., Tanaka, T., Terauchi, T., Morita, M., Kimijima, K., Sato, I., Shoji, W., Nakamura, Y., Tsukada, T., Tsunoda, T., Hayashi, G., Kanoh, N., & Nakata, M. (2003). Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments. Tetrahedron Letters, 44(42), 7747-7751. https://doi.org/10.1016/j.tetlet.2003.08.083

Terauchi, T, Tanaka, T, Terauchi, T, Morita, M, Kimijima, K, Sato, I, Shoji, W, Nakamura, Y, Tsukada, T, Tsunoda, T, Hayashi, G, Kanoh, N & Nakata, M 2003, 'Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments', Tetrahedron Letters, vol. 44, no. 42, pp. 7747-7751. https://doi.org/10.1016/j.tetlet.2003.08.083

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abstract = "Coupling of the C1-C14 (AB) crotylstannane with the C15-C28 (CD) aldehyde followed by stereochemical arrangements gave the C1-C28 (ABCD) fragment of altohyrtin C. The C29-C44 (EF) fragment was also prepared. The syntheses of these two fragments, both of which were identical with those prepared by the Smith group, constitute a formal total synthesis of altohyrtin C.",

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doi = "10.1016/j.tetlet.2003.08.083",

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

T2 - Construction of fully elaborated ABCD and EF fragments

AU - Terauchi, Takeshi

AU - Tanaka, Taisaku

AU - Terauchi, Taro

AU - Morita, Masataka

AU - Kimijima, Kyoko

AU - Sato, Ippei

AU - Shoji, Wataru

AU - Nakamura, Yasuhiro

AU - Tsukada, Tomoharu

AU - Tsunoda, Takashi

AU - Hayashi, Gouichirou

AU - Kanoh, Naoki

AU - Nakata, Masaya

PY - 2003/10/13

Y1 - 2003/10/13

N2 - Coupling of the C1-C14 (AB) crotylstannane with the C15-C28 (CD) aldehyde followed by stereochemical arrangements gave the C1-C28 (ABCD) fragment of altohyrtin C. The C29-C44 (EF) fragment was also prepared. The syntheses of these two fragments, both of which were identical with those prepared by the Smith group, constitute a formal total synthesis of altohyrtin C.

AB - Coupling of the C1-C14 (AB) crotylstannane with the C15-C28 (CD) aldehyde followed by stereochemical arrangements gave the C1-C28 (ABCD) fragment of altohyrtin C. The C29-C44 (EF) fragment was also prepared. The syntheses of these two fragments, both of which were identical with those prepared by the Smith group, constitute a formal total synthesis of altohyrtin C.

KW - Altohyrtins

KW - Crotylstannanes

KW - Spongistatins

KW - Stereoselective synthesis

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Formal total synthesis of altohyrtin C (spongistatin 2). Part 2: Construction of fully elaborated ABCD and EF fragments

Abstract

Keywords

ASJC Scopus subject areas

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