Document Detail

The total synthesis of manzamine A and related alkaloids.
MedLine Citation:
PMID:  23039372     Owner:  NLM     Status:  Publisher    
Total syntheses of three structurally complex marine natural products manzamine A, ircinol A, ircinal A are reported. The route pivoted on the construction of a late stage protecting group-free pentacyclic enol triflate coupling partner, from which all three family members were divergently accessed via palladium catalyzed reactions. The rapid synthesis of this key pentacyclic enol triflate was achieved by a highly convergent union of 5 fragments through a stereoselective Michael addition, a 3-component nitro-Mannich lactamization cascade, an unprecedented and highly stereoselective reductive nitro-Mannich cyclization cascade, a stereoselective organometallic addition and a Z-selective alkene ring-closing metathesis. Altogether this chemistry has allowed the shortest synthetic route to date for manzamine A (18 step longest linear sequence) via a late stage diversification point that is ideal for future manzamine A analogue synthesis.
Pavol Jakubec; Alison Hawkins; Wolfgang Felzmann; Darren J Dixon
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-7
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-8     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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