Literature DB >> 11112565

'Upenamide: An unprecedented macrocyclic alkaloid from the Indonesian sponge Echinochalina sp.

J I Jiménez1, G Goetz, C M Mau, W Y Yoshida, P J Scheuer, R T Williamson, M Kelly.   

Abstract

'Upenamide (1) represents a new class of macrocyclic marine alkaloid possessing both spirooxaquinolizidinone and hemiaminal ring systems. It was isolated from the Indonesian sponge Echinochalina sp. The gross structure of 1 was elucidated by spectroscopic methods and accurate mass measurements. A suggestion is made as to its biogenetic origin.

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Year:  2000        PMID： 11112565     DOI： 10.1021/jo000789w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  7 in total

Review 1.  Status and perspective of sponge chemosystematics.

Authors:  Dirk Erpenbeck; Rob W M van Soest
Journal:  Mar Biotechnol (NY)       Date:  2006-07-03       Impact factor: 3.619

2.  Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction.

Authors:  Zhushou Luo; Katherine Peplowski; Gary A Sulikowski
Journal:  Org Lett       Date:  2007-11-01       Impact factor: 6.005

3.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

4.  Diastereoselective One Pot Five-Component Reaction toward 4-(Tetrazole)-1,3-Oxazinanes.

Authors:  Ajay L Chandgude; Daniele Narducci; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Alexander Dömling
Journal:  RSC Adv       Date:  2017-10-26       Impact factor: 3.361

5.  A concise Diels-Alder strategy leading to congeners of the ABC ring system of the marine alkaloid 'upenamide.

Authors:  Marta E Wenzler; Bruce J Melancon; Gary A Sulikowski
Journal:  Tetrahedron Lett       Date:  2016-06-07       Impact factor: 2.415

Review 6.  A Soft Spot for Chemistry-Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution.

Authors:  Adrian Galitz; Yoichi Nakao; Peter J Schupp; Gert Wörheide; Dirk Erpenbeck
Journal:  Mar Drugs       Date:  2021-08-04       Impact factor: 5.118

7.  Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides.

Authors:  Pengcheng Wang; Ruirui Yu; Sajjad Ali; Zhengshen Wang; Zhigang Liu; Jinming Gao; Huaiji Zheng
Journal:  Molecules       Date:  2021-05-17       Impact factor: 4.411
  7 in total

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