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Nine-step enantioselective total synthesis of (+)-minfiensine.

ABSTRACT: An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

SUBMITTER: Jones SB

PROVIDER: S-EPMC2758560 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Nine-step enantioselective total synthesis of (+)-minfiensine.

Jones Spencer B SB Simmons Bryon B MacMillan David W C DW

Journal of the American Chemical Society 20090901 38

An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% ove ...[more]

PMID: 19725517

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