Total synthesis of a macrocyclic lactone antibiotic A26771B and its isomers using carbohydrates.

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概要

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• Total synthesis and antibacterial activities of a macrocyclic lactone antibiotic A26771B (<B>1</B>) and all its isomers (<B>2</B>, <B>3</B>, and <B>4</B>) are discussed. The starting 8,9,10,12-tetra-<I>O</I>-benzyl-2,3,4,5,11-pentadeoxy-<I>aldehydo</I>-D-<I>xylo</I>-(<I>E</I>)-6-dcdecenose derived from D-glucose reacted with racemic Wittig reagent, (3-hydroxybutyl)triphenylphosphonium iodide to give 1,3,4,5-tetra-<I>O</I>-benzyl-2,8,9,10,11,14,16-heptadeoxy-DL-<I>glycero</I>-L-<I>xylo</I>-hexadeca-6,12-dienitol, which was in turn converted into methyl 15-<I>O</I>-acetyl-6,7,8,9,10,11,12,13,14,16 -decadeoxy-4,5-<I>O</I>-isopropylidene-DL-<I>glycero</I>-L-<I>threo</I>-(<I>E</I>)-2-hexadecenonate (<B>13</B>) through effective oxidation and β-elimination. Saponification followed by Yamaguchi's lactonization of <B>13</B> afforded two diastereomeric 16-membered-ring lactones which were converted into (5<I>S</I>, 15<I>R</I>)-A26771B (<B>1</B>) and its (5<I>S</I>, 15<I>S</I>-diastereomer (<B>2</B>) by successive deacetonation, selective succinylation and oxidation. The other starting 2,3,4,6-tetra-<I>O</I>-benzyl-5-deoxy-<I>aldehydo</I>-D-<I>lyxo</I>-hexose, which was prepared from 2-deoxy-D-glucose, reacted with a Wittig reagent to give 8,9,10,12-tetra-<I>O</I>-benzyl-2,3,4,5,11-pentadeoxy-<I>aldehydo</I>-D-<I>lyxo</I>-6-dodecenose (<B>20</B>) followed by hydrol ysis. Similar reaction sequence from <B>20</B> with the aforesaid series for <B>1</B> and <B>2</B> afforded the (5<I>R</I>, 15<I>R</I>)-isomer (<B>3</B>) and (5<I>R</I>, 15<I>S</I>)-isomer (<B>4</B>).

• 公益社団法人 日本化学会の論文

著者

• Tatsuta Kuniaki

  Department Of Applied Chemistry Faculty Of Science And Technology Keito University

• Kinoshita Mitsuhiro

  Department of Applied Chemistry Engineering Faculty of Keio University

• Kanemura Yoshinobu

  Department of Applied Chemistry, Faculty of Science and Technology, Keio University

• Amemiya Yoshiya

  Department of Applied Chemistry, Faculty of Science and Technology, Keio University

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