Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

Tohru Oishi; Kouichiro Ootou; Hajime Shibata; Michio Murata

doi:10.1016/j.tetlet.2010.03.011

Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

Tohru Oishi, Kouichiro Ootou, Hajime Shibata, Michio Murata

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

4 Citations (Scopus)

Abstract

Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF.

Original language	English
Pages (from-to)	2600-2602
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2010.03.011
Publication status	Published - May 12 2010
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.03.011

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abstract = "Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF.",

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T1 - Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

AU - Oishi, Tohru

AU - Ootou, Kouichiro

AU - Shibata, Hajime

AU - Murata, Michio

PY - 2010/5/12

Y1 - 2010/5/12

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AB - Stereoselective synthesis of the chemoattractant sperm-activating and attracting factor (SAAF), isolated from the eggs of the ascidian Ciona intestinalis, was achieved via reductive 1,3-transposition of an allylic alcohol and the axial opening of an epoxide as key steps. This second-generation synthesis improved the total yield of SAAF over that of the first-generation synthesis and provided a key intermediate for synthesizing molecular probes of SAAF.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 19

ER -

Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

Abstract

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