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August 25, 2000Organic Letters

Total Synthesis of the Marine Alkaloid (−)-Lepadin B

Tetsuji Ozawa Sakae Aoyagi Chihiro Kibayashi

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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.

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Ozawa et al. (2000) studied this question.

synapsesocial.com/papers/6a95c9ccfdfcc8452d5142b1 https://doi.org/10.1021/ol000153r

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