345897-03-2Relevant academic research and scientific papers
Total synthesis of the marine alkaloids (-)-lepadins A, B, and C based on stereocontrolled intramolecular acylnitroso-diels-alder reaction
Ozawa,Aoyagi,Kibayashi
, p. 3338 - 3347 (2007/10/03)
The first syntheses of (-)-lepadins A and C, as well as a new synthesis of (-)-lepadin B, have been achieved from commercially available (S)-malic acid. The methodology is based on an intramolecular hetero-Diels-Alder reaction of the acylnitroso compound, affording the bicyclic oxazino lactam with trans selectivity, which was converted to the cis-decahydroquinoline via asymmetric enolate hydroxylation followed by intramolecular aldol cyclization. The total syntheses proceed by employing cis-decahydroquinoline bearing the (E)-iodoalkenyl group as the common key intermediate, which underwent a convergent coupling with the (E)-hexenyl unit via a palladium-catalyzed Suzuki cross-coupling reaction for the elaboration of the octadienyl side chain at the C5 position.
Total synthesis of the marine alkaloid (-)-lepadin B.
Ozawa,Aoyagi,Kibayashi
, p. 2955 - 2958 (2007/10/03)
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 t
