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PMID: 21846138 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Scalable, stereocontrolled total syntheses of (±)-axinellamines A and B.

Journal of the American Chemical Society ·Vol. 133 ·No. 35 ·2011-09-07 ·Pages 13922-5

Su S, Rodriguez RA, Baran PS

Abstract

The development of a simple, efficient, scalable, and stereocontrolled synthesis of a common intermediate en route to the axinellamines, massadines, and palau'amine is reported. This completely new route was utilized to prepare the axinellamines on a gram scale. In a more general sense, three distinct and enabling methodological advances were made during these studies: (1) an ethylene glycol-assisted Pauson-Khand cycloaddition reaction, (2) a Zn/In-mediated Barbier-type reaction, and (3) a TfNH(2)-assisted chlorination-spirocyclization.

MeSH Terms
Chemistry Techniques, Synthetic/economics,methods Guanidines/chemical synthesis Imidazoles/chemical synthesis Pyrroles/chemical synthesis Spiro Compounds/chemical synthesis Stereoisomerism
Chemicals
Guanidines Imidazoles Pyrroles Spiro Compounds axinellamine massadine palau'amine
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Su Shun
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
Rodriguez Rodrigo A
Baran Phil S
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18 references, click to expand
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Article Info
Journal
Journal of the American Chemical Society
Abbr.
J Am Chem Soc
ISSN
1520-5126
DOI
10.1021/ja206191g
Published
2011-09-07
Epub
2011-00-16
Pages
13922-5
Language
English
Region
United States
NLM ID
7503056
PMCID
PMC3164937
Subset
IM
Grants
NCI NIH HHS · R01 CA134785 · United States
NCI NIH HHS · R01 CA134785-02 · United States
NIGMS NIH HHS · R01 GM073949 · United States
NIGMS NIH HHS · GM-073949 · United States
External Links
PubMed source DOI: 10.1021/ja206191g PMC Full Text View journal details
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