Literature DB >> 12633090

Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration.

Kanako Hirai1, Hidenori Ooi, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama.   

Abstract

[reaction: see text] The first total synthesis of (+/-)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished based on Cr(II)/Ni(II)-mediated reaction of the aldehyde containing the citric acid moiety and the long-chain triflate, and the relative configuration of this natural product was determined.

Entities:  

Year:  2003        PMID： 12633090     DOI： 10.1021/ol0275264

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


  6 in total

1.  Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.

Authors:  Gary E Keck; Dennie S Welch; Paige K Vivian
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

2.  Preparation of the 5/5-spiroketal of the ritterazines.

Authors:  Douglass F Taber; Jean-Michel Joerger
Journal:  J Org Chem       Date:  2007-03-31       Impact factor: 4.354

3.  Three-component coupling approach to trachyspic acid.

Authors:  Daniel C Schmitt; Leighann Lam; Jeffrey S Johnson
Journal:  Org Lett       Date:  2011-08-31       Impact factor: 6.005

4.  Synthetic Studies Toward Bryostatin 1: Preparation of a C(1)-C(16) Fragment by Pyran Annulation.

Authors:  Gary E Keck; Dennie S Welch; Yam B Poudel
Journal:  Tetrahedron Lett       Date:  2006-11-20       Impact factor: 2.415

5.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

Review 6.  Asymmetric synthesis of naturally occurring spiroketals.

Authors:  B Rama Raju; Anil K Saikia
Journal:  Molecules       Date:  2008-08-28       Impact factor: 4.411
  6 in total

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