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1.
Chem Pharm Bull (Tokyo) ; 64(7): 800-4, 2016.
Article in English | MEDLINE | ID: mdl-27373634

ABSTRACT

Conversion of readily available vindoline to 11-mesyloxytabersonine, a versatile synthetic intermediate for indole alkaloids, has been achieved by a 9-step sequence in 39% overall yield.


Subject(s)
Indole Alkaloids/chemical synthesis , Vinblastine/analogs & derivatives , Indole Alkaloids/chemistry , Molecular Conformation , Vinblastine/chemistry
2.
J Am Chem Soc ; 136(18): 6598-601, 2014 May 07.
Article in English | MEDLINE | ID: mdl-24749477

ABSTRACT

The first asymmetric total synthesis of lepenine has been accomplished. The synthesis features a tethered intramolecular Diels-Alder reaction, an intramolecular Mannich reaction, and a Diels-Alder reaction between an ortho-quinone monoketal and ethylene, resulting in stereoselective construction of the unique hexacyclic system.


Subject(s)
Alkaloids/chemical synthesis , Alkaloids/chemistry , Stereoisomerism
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