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Total synthesis of the marine alkaloid (-)-lepadin B
T Ozawa1, S Aoyagi, C Kibayashi
1School of Pharmacy, Tokyo University of Pharmacy & Life Science, Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Organic Letters
|September 15, 2000
Abstract:
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.