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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2271-2278
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7172
A Formal Total Synthesis of (+)-Galactostatin via a Tetrahydroxynorleucine Derivative

Mitsunori Kirihata,* Yoshinobu Nakao, Masahiro Mori, and Itsuo Ichimoto

*Department of Applied Biochemistry, College of Agriculture, University of Osaka Prefecture, 1-1 Gakuencho, Sakai, Osaka 593, Japan

Abstract

(2S,3S,4S,5R)-2,3:4,6-Bis(isopropylidenedioxy)-5-[[(p-methoxybenzyloxy)carbonyl]amino]hexan-1-ol (14), a synthetic intermediate for (+)-galactostatin (1), has been synthesized starting from (+)-diethyl tartarate using the aldol-type condensation of methyl isocyanoacetate (2) with 4-O-benzyl-2,3-O-isopropyliden-L-threose (4) via a 3,4,5,6-tetrahydroxynorleucine derivative (8) as a key reaction.