Literature DB >> 24050750

Synthetic studies toward the citrinadin A and B core architecture.

Devon A Mundal1, Richmond Sarpong.   

Abstract

The core architecture of the citrinadin alkaloids has been prepared in racemic form by utilizing a strategy that exploits the alkylation of 2-methoxypyridines. An initially planned indolizidine to quinolizidine transformation to build the D/E rings was unsuccessful. Success was ultimately gained by a direct alkylation to establish the citrinadin core architecture.

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Year:  2013        PMID： 24050750      PMCID： PMC3829995          DOI： 10.1021/ol402177a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

1.  Tricyclic alkaloid core structures assembled by a cyclotrimerization-coupled intramolecular nucleophilic substitution reaction.

Authors:  Andrew L McIver; Alexander Deiters
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

2.  Total synthesis of alkaloid (+/-)-G. B. 13 using a Rh(I)-catalyzed ketone hydroarylation and late-stage pyridine reduction.

Authors:  Kimberly K Larson; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

3.  Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.

Authors:  Vishnumaya Bisai; Richmond Sarpong
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

5.  An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B.

Authors:  Ke Kong; John A Enquist; Monica E McCallum; Genessa M Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L Wood
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

6.  Total synthesis of the tricyclic marine alkaloids (-)-lepadiformine, (+)-cylindricine c, and (-)-fasicularin via a common intermediate formed by formic acid-induced intramolecular conjugate azaspirocyclization.

Authors:  Hideki Abe; Sakae Aoyagi; Chihiro Kibayashi
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

7.  Absolute stereochemistry of citrinadins a and B from marine-derived fungus.

Authors:  Takao Mugishima; Masashi Tsuda; Yuu Kasai; Haruaki Ishiyama; Eri Fukushi; Jun Kawabata; Masayuki Watanabe; Kenichi Akao; Jun'ichi Kobayashi
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

8.  Unified strategy for the synthesis of the "miscellaneous" lycopodium alkaloids: total synthesis of (+/-)-lyconadin A.

Authors:  Alakesh Bisai; Scott P West; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

9.  Concise, stereoselective approach to the spirooxindole ring system of citrinadin A.

Authors:  Martin Pettersson; Daniel Knueppel; Stephen F Martin
Journal:  Org Lett       Date:  2007-10-06       Impact factor: 6.005

10.  PF1270A, B and C, novel histamine H3 receptor ligands produced by Penicillium waksmanii PF1270.

Authors:  Nobuaki Kushida; Naoko Watanabe; Takako Okuda; Fumikazu Yokoyama; Yasuhiro Gyobu; Takashi Yaguchi
Journal:  J Antibiot (Tokyo)       Date:  2007-11       Impact factor: 2.649
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  2 in total

1.  Pyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A.

Authors:  Xianglin Yin; Kaiqing Ma; Ying Dong; Mingji Dai
Journal:  Org Lett       Date:  2020-06-17       Impact factor: 6.005

2.  Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.

Authors:  Zhiguo Bian; Christopher C Marvin; Martin Pettersson; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419
  2 in total

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