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The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form

✍ Scribed by Shigekazu Sasaki; Yasumasa Hamada; Takayuki Shioiri

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 216 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00411-6

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✦ Synopsis

The title acid, a component of microsclerodermins of marine sponge origin having five consecutive stereogenic centers, was efficiently synthesized as its protected form 1 from the alcohol 5 utilizing the stereoselective addition of anisole to the acetylenic triple bond and the anti-aldol reaction as key steps.

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