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

2 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

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All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Oishi, T., Ootou, K., Shibata, H., & Murata, M. (2010). Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis. Tetrahedron Letters, 51(19), 2600-2602. https://doi.org/10.1016/j.tetlet.2010.03.011

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Access to Document

10.1016/j.tetlet.2010.03.011