Formal Synthesis of Squalamine from Desmosterol

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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Veröffentlicht in:	Chemical & Pharmaceutical Bulletin 2003, Vol.51(10), pp.1177-1182
Hauptverfasser:	Okumura, Kazuo, Nakamura, Yutaka, Takeuchi, Seiji, Kato, Isao, Fujimoto, Yoshinori, Ikekawa, Nobuo
Format:	Artikel
Sprache:	eng
Schlagworte:	antibacterial Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Cholestanols - chemical synthesis Cholestanols - metabolism Desmosterol - chemistry Desmosterol - metabolism Medical sciences natural product Pharmacology. Drug treatments squalamine sterol
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Beschreibung
Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.51.1177