Total synthesis of the marine alkaloid (-)-lepadin B.
An enantioselective total synthesis of (-)-lepadin B has been developed starting from (2S,4S)-2,4-O-benzylidene-2, 4-dihydroxybutanal. The key steps in the synthesis include the use of an aqueous intramolecular acylnitroso Diels-Alder reaction to afford the trans-1,2-oxazinolactam and Suzuki cross-coupling reaction to elaborate the (E,E)-octadienyl unit.
Ozawa
T
T
School of Pharmacy, Tokyo University of Pharmacy & Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Aoyagi
S
S
Kibayashi
C
C
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D010986:Platyhelminths / Q000737:chemistry / Q000378:metabolism; D011804:Quinolines; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry / Q000378:metabolism
D000470:Alkaloids; D006574:Heterocyclic Compounds, 2-Ring; D011804:Quinolines; C414923:lepadin B