Total synthesis of spicamycin

Tamotsu Suzuki, Sayaka T. Suzuki, Iwao Yamada, Yoshiaki Koashi, Kazue Yamada, Noritaka Chida

研究成果: Article査読

69 被引用数 (Scopus)

抄録

The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.

本文言語English
ページ(範囲)2874-2880
ページ数7
ジャーナルJournal of Organic Chemistry
67
9
DOI
出版ステータスPublished - 2002 5月 3

ASJC Scopus subject areas

  • 有機化学

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