A concise approach to the tricyclic core of the cytotoxic marine alkaloid madangamine A

Journal of Organic Chemistry

Volumn 62, Issue 7, 1997, Pages 1920-1921

  Matzanke, Norbert ^a   Gregg, Robert J ^a   Weinreb, Steven M ^a   Parvez, Masood ^b  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYTOTOXIC AGENT; MADANGAMINE A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030944697     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970208b     Document Type: Article

References (18)

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6. SES = β-(trimethylsilyl)ethanesulfonyl. Prepared from commercially available aminoacetaldehyde dimethyl acetal and SES-Cl: Weinreb, S. M.; Demko, D. M.; Lessen, T. A.; Demers, J. P. Tetrahedron Lett. 1986, 27, 2099. Weinreb, S. M.; Chase, C. E.; Wipf, P.; Venkatraman, S. Org. Synth., in press.
7. SES = β-(trimethylsilyl)ethanesulfonyl. Prepared from commercially available aminoacetaldehyde dimethyl acetal and SES-Cl: Weinreb, S. M.; Demko, D. M.; Lessen, T. A.; Demers, J. P. Tetrahedron Lett. 1986, 27, 2099. Weinreb, S. M.; Chase, C. E.; Wipf, P.; Venkatraman, S. Org. Synth., in press.
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9. (a) The cyeloaddition has been run on a scale to produce about 1 g of adduct using a Leco Model PG-200-HPC apparatus.
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14. Imine 12 could be reduced in situ with sodium borohydride to afford the W-allyl analog of amine 14.
15. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
16. Hydroboration of various N-protected derivatives of primary amine 14 proceeded in low yields.
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