Formal Synthesis of Squalamine from Desmosterol

Kazuo Okumura; Yutaka Nakamura; Seiji Takeuchi; Isao Kato; Yoshinori Fujimoto; Nobuo Ikekawa

doi:10.1248/cpb.51.1177

Notes

Formal Synthesis of Squalamine from Desmosterol

Kazuo Okumura, Yutaka Nakamura, Seiji Takeuchi, Isao Kato, Yoshinori Fujimoto, Nobuo Ikekawa

Author information

Keywords: sterol, squalamine, antibacterial, natural product

JOURNAL FREE ACCESS

2003 Volume 51 Issue 10 Pages 1177-1182

DOI https://doi.org/10.1248/cpb.51.1177

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Abstract

The key intermediate to squalamine, (5α,7α,24R)-7,24-dihydroxy-cholestan-3-one, was synthesized from the 3-O-acetyl-24R,25-dihydroxy derivative of desmosterol via 10 steps in 16% overall yield and squalamine was also prepared via two further steps in 7.4% total yield from the desmosterol derivative.

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