Literature DB >> 19670853

Total synthesis of irciniastatin A (Psymberin).

Michael T Crimmins1, Jason M Stevens, Gregory M Schaaf.   

Abstract

The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.

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Year:  2009        PMID： 19670853      PMCID： PMC2752752          DOI： 10.1021/ol901655e

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


  26 in total

1.  General Synthesis of alpha-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.

Authors:  Vilas H. Dahanukar; Scott D. Rychnovsky
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

2.  Antineoplastic agents. 520. Isolation and structure of irciniastatins A and B from the Indo-Pacific marine sponge Ircinia ramosa.

Authors:  George R Pettit; Jun-Ping Xu; Jean-Charles Chapuis; Robin K Pettit; Larry P Tackett; Dennis L Doubek; John N A Hooper; Jean M Schmidt
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

3.  A convergent coupling strategy for the formation of polycyclic ethers: stereoselective synthesis of the BCDE fragment of brevetoxin A.

Authors:  Michael T Crimmins; Patrick J McDougall; Kyle A Emmitte
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

4.  Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products.

Authors:  Xin Jiang; Noelle Williams; Jef K De Brabander
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

5.  The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs.

Authors:  Xianhai Huang; Ning Shao; Robert Huryk; Anandan Palani; Robert Aslanian; Cynthia Seidel-Dugan
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

6.  Diphenylphosphoryl azide. A new convenient reagent for a modified Curtus reaction and for the peptide synthesis.

Authors:  T Shioiri; K Ninomiya; S Yamada
Journal:  J Am Chem Soc       Date:  1972-08-23       Impact factor: 15.419

7.  Titanium enolates of thiazolidinethione chiral auxiliaries: versatile tools for asymmetric aldol additions.

Authors:  M T Crimmins; K Chaudhary
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

8.  A formal synthesis of psymberin.

Authors:  Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-24       Impact factor: 6.005

9.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

Authors:  Leticia Ayala; Claudia G Lucero; Jan Antoinette C Romero; Sarah A Tabacco; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

10.  The total synthesis of psymberin.

Authors:  Xianhai Huang; Ning Shao; Anandan Palani; Robert Aslanian; Alexei Buevich
Journal:  Org Lett       Date:  2007-05-25       Impact factor: 6.005
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  9 in total

1.  Total synthesis of the cyanolide A aglycon.

Authors:  Michael R Gesinski; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2011-06-08       Impact factor: 15.419

2.  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

3.  Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Authors:  Ashutosh Pal; Zhenghong Peng; Paul T Schuber; Basvoju A Bhanu Prasad; William G Bornmann
Journal:  Tetrahedron Lett       Date:  2013-10-09       Impact factor: 2.415

4.  Temporary restraints to overcome steric obstacles: an efficient strategy for the synthesis of mycalamide B.

Authors:  John C Jewett; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

5.  Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Authors:  Yu Feng; Xin Jiang; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2012-10-04       Impact factor: 15.419

6.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

7.  Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin B.

Authors:  Chihui An; Jon A Jurica; Shawn P Walsh; Adam T Hoye; Amos B Smith
Journal:  J Org Chem       Date:  2013-04-12       Impact factor: 4.354

Review 8.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876

9.  Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents.

Authors:  Qi Liu; Chihui An; Karen TenDyke; Hongsheng Cheng; Young Yongchun Shen; Adam T Hoye; Amos B Smith
Journal:  J Org Chem       Date:  2016-02-16       Impact factor: 4.354
  9 in total

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