Concise enantioselective synthesis of ent-malbrancheamide B

Journal of the American Chemical Society

Volumn 131, Issue 12, 2009, Pages 4214-4215

  Frebault, Frederic ^a   Simpkins, Nigel S ^a   Fenwick, Ashley ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS;

ENANTIOSELECTIVE SYNTHESIS; ENOL ETHERS; FUNGAL METABOLITES; PROLINE DERIVATIVES; PYRUVIC ACID; SEM; SUBSTITUTED INDOLES;

ORGANIC ACIDS;

AMIDE; CALMODULIN INHIBITOR; HYDROXAMIC ACID; PARAHERQUAMIDE; PROLINE; PYRUVIC ACID; ALDEHYDE; ALKALOID; BICYCLO COMPOUND; BIOMIMETIC MATERIAL; CATION; ETHER DERIVATIVE; INDOLE ALKALOID; MALBRANCHEAMIDE; MALBRANCHEAMIDE B;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; FUNGUS; PROTECTION; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL MODEL; CHEMISTRY; METABOLISM; ORGANIC CHEMISTRY; PROCEDURES; STEREOISOMERISM;

ALDEHYDES; ALKALOIDS; AMIDES; BICYCLO COMPOUNDS; BIOMIMETIC MATERIALS; CATIONS; CHEMISTRY, ORGANIC; CYCLIZATION; ETHERS; FUNGI; HYDROXAMIC ACIDS; INDOLE ALKALOIDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 67849087069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900688y     Document Type: Article

References (18)

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9. This assumes that no bystander asymmetric centers are present; see ref 1 for examples.
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14. More usual ethers, including OMe and OPMB types, were tried first, but this system appears to be unexpectedly stable toward acidic reagents, presumably because of the push-pull nature of the extended conjugated indole carboxamide. Forcing conditions resulted in destruction of the starting materials with no constructive cyclization.
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18. We thank Professor R. M. Williams (Colorado State University) and Professor R. Mata (Instituto de Biologia, Universidad Nacional Autónoma de Méixico) for their assistance in clarifying the identity of our synthetic sample.