Art

J-GLOBAL ID：200902212385260597   Reference number：08A0372770

First total synthesis and absolute configuration of naturally occurring (-)-hyacinthacine A₇ and its (-)-1-epi-isomer

天然に存在する(-)-ヒアシンタシンA₇とその(-)-1-epi-異性体の初全合成及び絶対配置

Author (6)： IZQUIERDO Isidoro (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP) ,  PLAZA Maria T. (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP) ,  TAMAYO Juan A. (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP) ,  YANEZ Victor (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP) ,  LO RE Daniele (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP) ,  SANCHEZ-CANTALEJO Fernando (Dep. of Medicinal and Organic Chemistry, Fac. of Pharmacy, Univ. of Granada, 18071 Granada, ESP)
Material： Tetrahedron  (Tetrahedron Symposia-in-Print)
Volume： 64  Issue： 20  Page： 4613-4618  Publication year： May. 12, 2008 
JST Material Number： E0234A  ISSN： 0040-4020  Document type： Article
Article type： 原著論文  Country of issue： United Kingdom (GBR)  Language： ENGLISH (EN)

Thesaurus term： *pyrrolizidine alkaloid ,  Liliaceae ,  secondary metabolite ,  enzyme inhibitor ,  glycosidic linkage hydrolase ,  epimer ,  total synthesis ,  asymmetric synthesis ,  *Wittig reaction(coupling) ,  *annulation ,  epimerization ,  deprotection ,  absolute configuration ,  NOESY

JST classification (3)： Alkaloids  (CF10030D) ,  Plant biochemistry  (EH01050J) ,  Synthesis of drugs  (GV01030F)

Substance index (8)： Hyacinthacine A₇ ,  (2R)-2α-(Hydroxymethyl)-3β-(benzoyloxy)-4α-(benzyloxy)-5-(tert-butyldiphenylsiloxymethyl)pyrrolidine-1-carboxylic acid benzyl ester ,  (2S)-2α-Formyl-3β-(benzoyloxy)-4α-(benzyloxy)-5-(tert-butyldiphenylsiloxymethyl)pyrrolidine-1-carboxylic acid benzyl ester ,  (2R)-2α-[(E)-3-Oxo-1-butenyl]-3β-(benzoyloxy)-4α-(benzyloxy)-5-(tert-butyldiphenylsiloxymethyl)pyrrolidine-1-carboxylic acid benzyl ester ,  (1R,7aβ)-1β-(Benzoyloxy)-2α-(benzyloxy)-3β-(tert-butyldiphenylsiloxymethyl)-5β-methylhexahydro-1H-pyrrolizine ,  (1R,7aβ)-1β-(Benzoyloxy)-2α-(benzyloxy)-3β-(tert-butyldiphenylsiloxymethyl)-5α-methylhexahydro-1H-pyrrolizine ,  (1R,7aβ)-2α-(Benzyloxy)-3β-(tert-butyldiphenylsiloxymethyl)-5α-methylhexahydro-1H-pyrrolizine-1β-ol ,  (1R,7aβ)-3β-(Hydroxymethyl)-5β-methylhexahydro-1H-pyrrolizine-1β,2α-diol

Terms in the title (3)： EPI ,  異性体 ,  全合成