Enantioselective synthesis of lepadins A-D from a phenylglycinol-derived hydroquinolone lactam.
نویسندگان
چکیده
The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.
منابع مشابه
Stereoselective synthesis of (-)-lepadins A-C.
A concise synthesis of the marine alkaloids (-)-lepadins A-C from a phenylglycinol-derived tricyclic lactam is reported. Key steps from the stereochemical standpoint involve stereoselective cyclocondensation, double bond hydrogenation, oxazolidine opening, hydroboration-oxidation, and Horner-Wadsworth-Emmons reactions.
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عنوان ژورنال:
- Chemistry
دوره 21 36 شماره
صفحات -
تاریخ انتشار 2015