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Towards the total synthesis of keramaphidin B.

ABSTRACT: The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

SUBMITTER: Jakubec P

PROVIDER: S-EPMC4901993 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Towards the total synthesis of keramaphidin B.

Jakubec Pavol P Farley Alistair J M AJ Dixon Darren J DJ

Beilstein journal of organic chemistry 20160530

The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B. ...[more]

PMID: 27340496

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