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Divergent total syntheses of lyconadins A and C.

ABSTRACT: Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins?A and C have been developed. The synthesis of lyconadin?A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin?C. Both lyconadins?A and C were synthesized from a pivotal intermediate.

SUBMITTER: Yang Y

PROVIDER: S-EPMC4113559 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Divergent total syntheses of lyconadins A and C.

Yang Yang Y Haskins Christopher W CW Zhang Wandi W Low Pui Leng PL Dai Mingji M

Angewandte Chemie (International ed. in English) 20140305 15

Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate. ...[more]

PMID: 24596132

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