Synthesis of the glycosyl lactol moiety of halichoblelide

Yohsuke Satoh; Takashi Nakahata; Shigefumi Kuwahara

doi:10.1016/j.tet.2007.08.100

Synthesis of the glycosyl lactol moiety of halichoblelide

Yohsuke Satoh, Takashi Nakahata, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

4 Citations (Scopus)

Abstract

The enantioselective synthesis of the 2-deoxy-α-l-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected l-fucal as the key steps.

Original language	English
Pages (from-to)	11733-11737
Number of pages	5
Journal	Tetrahedron
Volume	63
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2007.08.100
Publication status	Published - 2007 Nov 19

Keywords

Cytotoxic
Enantioselective synthesis
Glycosidation
Halichoblelide

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2007.08.100

Cite this

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title = "Synthesis of the glycosyl lactol moiety of halichoblelide",

abstract = "The enantioselective synthesis of the 2-deoxy-α-l-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected l-fucal as the key steps.",

keywords = "Cytotoxic, Enantioselective synthesis, Glycosidation, Halichoblelide",

author = "Yohsuke Satoh and Takashi Nakahata and Shigefumi Kuwahara",

note = "Funding Information: We are grateful to Prof. Yamada (Osaka University of Pharmaceutical Sciences) for providing the copies of the NMR spectra of halichoblelide. We also thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).",

year = "2007",

month = nov,

day = "19",

doi = "10.1016/j.tet.2007.08.100",

language = "English",

volume = "63",

pages = "11733--11737",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis of the glycosyl lactol moiety of halichoblelide

AU - Satoh, Yohsuke

AU - Nakahata, Takashi

AU - Kuwahara, Shigefumi

N1 - Funding Information: We are grateful to Prof. Yamada (Osaka University of Pharmaceutical Sciences) for providing the copies of the NMR spectra of halichoblelide. We also thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 19380065).

PY - 2007/11/19

Y1 - 2007/11/19

N2 - The enantioselective synthesis of the 2-deoxy-α-l-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected l-fucal as the key steps.

AB - The enantioselective synthesis of the 2-deoxy-α-l-fucosyl lactol moiety of halichoblelide, a potent cytotoxin isolated from an actinomycete of marine origin, was achieved using a diastereoselective addition of a dithianyl anion to a chiral aldehyde intermediate and a stereoselective glycosidation of a hydroxy lactone intermediate derived from the addition product with a protected l-fucal as the key steps.

KW - Cytotoxic

KW - Enantioselective synthesis

KW - Glycosidation

KW - Halichoblelide

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U2 - 10.1016/j.tet.2007.08.100

DO - 10.1016/j.tet.2007.08.100

M3 - Article

AN - SCOPUS:34948906776

VL - 63

SP - 11733

EP - 11737

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 47

ER -

Synthesis of the glycosyl lactol moiety of halichoblelide

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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