+ Site Statistics
References:
52,654,530
Abstracts:
29,560,856
PMIDs:
28,072,755
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

On the structure of palau'amine: evidence for the revised relative configuration from chemical synthesis



On the structure of palau'amine: evidence for the revised relative configuration from chemical synthesis



Journal of the American Chemical Society 129(42): 12896-12900



Hexacyclic congeners 3 and 4 of palau'amine, which incorporate both guanidine functional groups and have the cis configuration of the azabicyclo[3.3.0]octane core, are prepared in 14 steps from cycloadduct 6. Synthetic access to these analogues allows the first direct comparison of NMR data for hexacyclic diguanidine structures having the originally proposed cis-azabicyclo[3.3.0]octane fragment with data for natural alkaloids of the palau'amine family. This comparison provides convincing evidence in favor of the recently proposed structural revision of these marine alkaloids, fully supporting the trans configuration of the central azabicyclo[3.3.0]octane ring system of palau'amine and congeners.

(PDF emailed within 0-6 h: $19.90)

Accession: 021491623

Download citation: RISBibTeXText

PMID: 17902668

DOI: 10.1021/ja074939x


Related references

Spirastrellolide A: revised structure, progress toward the relative configuration, and inhibition of protein phosphatase 2A. Organic Letters 6(15): 2607-2610, 2004

Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine. Angewandte Chemie 47(36): 6821-6824, 2008

Structural assignment of tetrabromostyloguanidine: does the relative configuration of the palau'amines need revision?. Angewandte Chemie 46(13): 2320-2324, 2007

The revised structure, total synthesis, and absolute configuration of streptophenazine A. Organic Letters 13(20): 5436-5439, 2011

Revised structure, synthesis and absolute configuration of hippospongic acid A. Tetrahedron Letters 39(42): 7745-7746, Oct 15, 1998

Revised structure, total synthesis, and absolute configuration of kopeolin and kopeolone. Journal of Organic Chemistry 79(5): 2268-2273, 2014

Total synthesis of palau'amine. Angewandte Chemie 49(6): 1095-1098, 2010

Synthesis of the C9-C25 fragment of L-755,807. Evidence for the relative configuration of the side-chain. Tetrahedron Letters 39(33): 6033-6036, 1998

Toward palau'amine: Hg(OTf)2-catalyzed synthesis of the cyclopentane core. Chemistry 15(27): 6560-6563, 2009

Total synthesis of the marine alkaloid palau'amine. Angewandte Chemie 49(17): 2972-2974, 2010

Exploring symmetry-based logic for a synthesis of palau'amine. Journal of Organic Chemistry 74(16): 5909-5919, 2010

Approach toward the total synthesis of orevactaene. 2. Convergent and stereoselective synthesis of the C18-C31 domain of orevactaene. Evidence for the relative configuration of the side chain. Journal of Organic Chemistry 67(15): 5176-5183, 2002

Evaluation Of Strategies For The Synthesis Of The Guanidine Hemiaminal Portion Of Palau'amine. Heterocycles 70: 557-570, 2006

Extending Pummerer reaction chemistry: studies in the palau'amine synthesis area. Journal of Organic Chemistry 76(12): 5042-5060, 2011

Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine. Angewandte Chemie 47(46): 8885-8888, 2008