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An end-game strategy for construction of the G-H-I rings of penitrem D, A tremorgenic indole alkaloid by Amos B. Smith III; Mitsuaki Ohta; William M. Clark; James W. Leahy is a Chemistry article available to read on EtoBox.

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Summery: A synthetic approach to the G-H-I ring system of per&rem D has heen developed In a modet study. To generate the requblte carbon framework, the Stork protocol was utilized for coupling of a scalemb metafkXnamine wlth an epoxide dedvedfmmD-g\_. Pyran ring fomwtbn was then effected vta BFg9E12pmmoted qdkatbn of a Mydroxy atty2c acelate. The tremorgenlc indole akaloids embody unusual, archttecturalty complex polycyclk skeleta and also present disttnctive bkbgbal profiles, mductng tr6imors in animals and poSSeSsing stgntfkant tnsectbkfal acttvtty.'~2 Prominent mernher6 of the class include the penitrem tremorgenk mycotoxins (la), ftr~t isolated from PenirMum cruafoaum,~ which cause severe neumbgiil dyshlnctbn In Itvestock, not unllke the symptoma observed in human disorders such as Wilson's disease and multiple sclerosis.3e~4~5 Subinine A and B (7 and 6L6 recently Isolated from the sclerotta of Aspergi//us su~hureus, Share the terminal G-l-l-l ring suh~tructures and 7 exhtts pronounced cytotoxklty toward human lung, breast, and colon carcinomas.6 Cur bng-standing interest in the constructbn of the lndole alkabld tremorgens7 has led to a penttrem D (4) synthetic venture.\* Herei

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Author

Amos B. Smith III; Mitsuaki Ohta; William M. Clark; James W. Leahy

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

1993

Language

EN

Field

Chemistry (Physical Sciences)