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Enantioselective total synthesis of (+)-amabiline.

ABSTRACT: The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features novel methodology to construct the unsaturated pyrrolizidine or (-)-supinidine core.

SUBMITTER: Senter TJ

PROVIDER: S-EPMC3359844 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Enantioselective total synthesis of (+)-amabiline.

Senter Timothy J TJ Fadeyi Olugbeminiyi O OO Lindsley Craig W CW

Organic letters 20120320 7

The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features novel methodology to construct the unsaturated pyrrolizidine or (-)-supinidine core. ...[more]

PMID: 22432912

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