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Literature DB >> 20831229

Enantioselective total synthesis of spirofungins A and B.

Michael T Crimmins¹, Elizabeth A O'Bryan.

Abstract

The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.

Entities: Chemical Disease Gene Species

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Year: 2010 PMID： 20831229 PMCID： PMC2950280 DOI： 10.1021/ol101961c

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

16 in total

1. Short synthesis of the 6,6-spiroketal cores of spirofungins A and B.

Authors: Luiz C Dias; Luciana G de Oliveira
Journal: Org Lett Date: 2004-07-22 Impact factor: 6.005

2. Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Authors: M T Crimmins; B W King; E A Tabet; K Chaudhary
Journal: J Org Chem Date: 2001-02-09 Impact factor: 4.354

3. Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.

Authors: Michael T Crimmins; Hamish S Christie; Kleem Chaudhary; Alan Long
Journal: J Am Chem Soc Date: 2005-10-12 Impact factor: 15.419

4. Synthesis of the spirofungin B core by a reductive cyclization strategy.

Authors: Thomas E La Cruz; Scott D Rychnovsky
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

5. An affinity probe for isolation of abscisic acid-binding proteins.

Authors: James M Nyangulu; Marek M Galka; Ashok Jadhav; Yuanzhu Gai; Cindy M Graham; Ken M Nelson; Adrian J Cutler; David C Taylor; Gary M Banowetz; Suzanne R Abrams
Journal: J Am Chem Soc Date: 2005-02-16 Impact factor: 15.419

6. Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities.

Authors: H Takahashi; H Osada; H Koshino; M Sasaki; R Onose; M Nakakoshi; M Yoshihama; K Isono
Journal: J Antibiot (Tokyo) Date: 1992-09 Impact factor: 2.649

7. Reveromycins, new inhibitors of eukaryotic cell growth. I. Producing organism, fermentation, isolation and physico-chemical properties.

Authors: H Takahashi; H Osada; H Koshino; T Kudo; S Amano; S Shimizu; M Yoshihama; K Isono
Journal: J Antibiot (Tokyo) Date: 1992-09 Impact factor: 2.649

Enantioselective total synthesis of spirofungins A and B.

1. Short synthesis of the 6,6-spiroketal cores of spirofungins A and B.

2. Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

3. Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.

4. Synthesis of the spirofungin B core by a reductive cyclization strategy.

5. An affinity probe for isolation of abscisic acid-binding proteins.

6. Reveromycins, new inhibitors of eukaryotic cell growth. II. Biological activities.

7. Reveromycins, new inhibitors of eukaryotic cell growth. I. Producing organism, fermentation, isolation and physico-chemical properties.

8. Reveromycins, new inhibitors of eukaryotic cell growth. III. Structures of reveromycins A, B, C and D.

9. Spirofungin, a new antifungal antibiotic from Streptomyces violaceusniger Tü 4113.

10. Total synthesis of apoptolidin A.

1. Synthesis of the C₁-C₁₇ fragment of the archazolids by complex cis-homodimer cross metathesis.

2. The Synthesis of 3-(R)- and 3-(S)-Hydroxyeicosapentaenoic Acid.