Total synthesis of hyacinthacine A1 and 3-epi-hyacinthacine A1.
[reaction: see text] Total synthesis of hyacinthacine A(1) and its epimer at C3 is described. The synthesis includes a stereocontrolled carboazidation of a chiral allylsilane as a key step. C-Si bond oxidation and reduction of the azide, with ring-closure, complete the total synthesis, which establishes the absolute configuration of 3.
Chabaud
Laurent
L
Laboratoire de Chimie Organique et Organométallique, Université Bordeaux-I, 351, Cours de la Libération, F-33405 Talence Cedex, France.
Landais
Yannick
Y
Renaud
Philippe
P
D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D019668:Liliaceae / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D011763:Pyrrolizidine Alkaloids; C508850:hyacinthacine A1; D006026:Glycoside Hydrolases