Literature DB >> 15796524

Total synthesis of cribrostatin IV: fine-tuning the character of an amide bond by remote control.

Collin Chan1, Richard Heid, Shengping Zheng, Jinsong Guo, Bishan Zhou, Takeshi Furuuchi, Samuel J Danishefsky.   

Abstract

We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).

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Year:  2005        PMID: 15796524     DOI: 10.1021/ja050203t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

1.  Antitumor activity of tetrahydroisoquinoline analogues 3-epi-jorumycin and 3-epi-renieramycin G.

Authors:  Jonathan W Lane; Alberto Estevez; Kyle Mortara; Ondine Callan; Jeffrey R Spencer; Robert M Williams
Journal:  Bioorg Med Chem Lett       Date:  2006-05-02       Impact factor: 2.823

Review 2.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

Review 3.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

Review 4.  Ecteinascidins. A review of the chemistry, biology and clinical utility of potent tetrahydroisoquinoline antitumor antibiotics.

Authors:  V H Le; M Inai; R M Williams; T Kan
Journal:  Nat Prod Rep       Date:  2015-02       Impact factor: 13.423

5.  Dragmacidin E synthesis studies. Preparation of a model heptacyclic core structure.

Authors:  Ken S Feldman; Paiboon Ngernmeesri
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

6.  Chemistry of Renieramycins. Part 14: Total Synthesis of Renieramycin I and Practical Synthesis of Cribrostatin 4 (Renieramycin H).

Authors:  Masashi Yokoya; Keiichiro Kobayashi; Mitsuhiro Sato; Naoki Saito
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118

  6 in total

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