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

doi:10.1016/S0040-4039(01)01069-3

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

Department of Applied Chemistry

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

19 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 language	English
Pages (from-to)	5505-5508
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(01)01069-3
Publication status	Published - 2001 Aug 6

Keywords

Altohyrtins
Spongistatins
Stereoselective synthesis
Weinreb coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(01)01069-3

Cite this

@article{05de4ae2580d4855a8000af316054138,

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

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.",

keywords = "Altohyrtins, Spongistatins, Stereoselective synthesis, Weinreb coupling",

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

year = "2001",

month = aug,

day = "6",

doi = "10.1016/S0040-4039(01)01069-3",

language = "English",

volume = "42",

pages = "5505--5508",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "32",

}

TY - JOUR

T1 - Synthetic studies on altohyrtins (spongistatins)

T2 - Synthesis of the C29-C44 (EF) portion

AU - Terauchi, Takeshi

AU - Morita, Masataka

AU - Kimijima, Kyoko

AU - Nakamura, Yasuhiro

AU - Hayashi, Gouichirou

AU - Tanaka, Taisaku

AU - Kanoh, Naoki

AU - Nakata, Masaya

PY - 2001/8/6

Y1 - 2001/8/6

N2 - 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.

AB - 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.

KW - Altohyrtins

KW - Spongistatins

KW - Stereoselective synthesis

KW - Weinreb coupling

UR - http://www.scopus.com/inward/record.url?scp=0035817299&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035817299&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)01069-3

DO - 10.1016/S0040-4039(01)01069-3

M3 - Article

AN - SCOPUS:0035817299

SN - 0040-4039

VL - 42

SP - 5505

EP - 5508

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this