Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines

Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines

フォーマット:

論文

責任表示:

Ohba, Masashi ; Mukaihira, Takafumi ; Fujii, Tozo

言語:

英語

出版情報:

日本薬学会, 1994-09-15

著者名:

掲載情報:

Chemical & pharmaceutical bulletin

ISSN:

0009-2363

巻:

42

通号:

9

開始ページ:

1784

終了ページ:

1790

バージョン:

publisher

概要:

Chiral syntheses of 3-methyl-5-(phenylthio)-L-histidine (8a) and 3-methyl-5-(1-naphthalenylthio)-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have been accomplished through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involved were methylation of 9, hydroxymethylation of 4-bromo-1-methyl-1H-imidazole (11), replacement of the 4-bromo group by an arylthio group in the aldehyde 14, and … introduction of a chiral α-amino acid moiety into the chlorides 17a and 17b by the 'bis-lactim ether' method. The synthesis of the 4-(4-methoxybenzyl)thio analogue 17c, carried out in a similar manner, concluded formal syntheses of ovothiols A and C (1 and 3). 続きを見る

URL:

http://hdl.handle.net/2297/7619

タイトル・著者・出版者が同じ資料

詳細

主題:	arylmethylation; arylthio-L-histidine chiral synthesis; bis-lactim ether; bromoimidazole N-methylation; hydroxymethylation; imidazole; imidazolium salt thermal N-demethylation
受理日:	1994-09-15

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1 論文 Synthetic studies on the starfish alkaloid imbricatine. Construction of an ent-imbricatine framework Ohba, Masashi, Imasho, M., Fujii, Tozo 日本薬学会	7 論文 Quinolizidines. XXXIII. A chiral synthesis of (-)-ophiorrhizine, a pentacyclic quaternary indole alkaloid from ophiorrhiza major RIDL Fujii, Tozo, Ohba, Masashi, Seto, Shigeki 日本薬学会
2 論文 Racemic and Chiral Syntheses of Some Indolo[2,3-a] Quinolizidine Alkaloids Through a "Lactim Etherroute" Fujii, Tozo, Ohba, Masashi （株）日本複素環化学研究所	8 論文 Quinolizidines. XIV. A racemic synthesis of 9-demethyltubulosine, an alkaloid isolated from Alangium vitiense Ohba, Masashi, Hayashi, Mitsuko, Fujii, Tozo 日本薬学会
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6 論文 Quinolizidines. VIII. Structure and Synthesis of the Alangium Alkaloid Alangicine : Syntheses of (±)- and (+)-Alangicines Fujii, Tozo, Yamada, Koichiro, Minami, Shinzaburo, Yoshifuji, Shigeyuki, Ohba, Masashi 日本薬学会	12 論文 Quinolizidines. XI. Structure determination of the Alangium alkaloid desmethylpsychotrine through synthetic incorporation of ethyl cincholoiponate into … Fujii, Tozo, Ohba, Masashi 日本薬学会