Total Synthesis of (+)‐Antimycin A<sub>3b</sub> on Solid Supports

Iijima, Yusuke; Kimata, Osamu; Decharin, Santida; Masui, Hisashi; Hirose, Yoichiro; Takahashi, Takashi

doi:10.1002/ejoc.201402430

Cited by 7 publications

(3 citation statements)

References 33 publications

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“…During the printing of issue 22/2014, Scheme on page 4727 of the original article 1 was inadvertently replaced by a different graphic not pertaining to the paper. The correct Scheme 3 is given below.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of (+)‐Antimycin A_3b on Solid Supports

Iijima¹,

Kimata²,

Decharin³

et al. 2014

Eur J Org Chem

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Section: Methodsmentioning

confidence: 99%

Total Synthesis of (+)‐Antimycin A_3b on Solid Supports

Iijima¹,

Kimata²,

Decharin³

et al. 2014

Eur J Org Chem

Self Cite

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“…Furthermore, the O ‐Thp, N ‐Fmoc protected version of Thr was used as part of interesting SPPS strategies described by Krishnamoorthy et al . and Iijima et al . for the total syntheses of callipeltin B and (+)‐antimycin A 3b , respectively.…”

Section: Thp Protection Of the Hydroxy Group (Serine And Threonine)mentioning

confidence: 99%

“…It has been reported that Ser and Thr hydroxyl side chains protected with Thp are deprotected under acidic conditions. In this regard, HCl, [41,46] TFA-containing cocktails (1, 2o r9 5% TFA), [47][48][49] TsOH [42] or PPTS [39,40,43,49] in alcoholic solvents have been reported to cleave the Thp group. Accordingly,w eh ave recently confirmed that Thp removalc an be achieved using 2% TFAi nC H 2 Cl 2 in the presence of scavengers.…”

Section: Removal Of the Protecting Groupmentioning

confidence: 99%

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

et al. 2017

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Tetrahydropyranyl (Thp) is recognized as a useful protecting group for alcohols in organic synthesis. It has several advantages, including low cost, ease of introduction, general stability to most non‐acidic reagents, it confers good solubility, and the ease with which it can be removed if the functional group it protects requires manipulation. However, little attention has been paid to Thp in peptide chemistry. Provided here is a concise analysis of the Thp protection of various amino acid functionalities (OH, SH, NH and COOH) and its application to peptide synthesis. Thp is a useful moiety for the side‐chain protection of serine, threonine and cysteine and is suitable for the Fmoc/tBu solid‐phase peptide synthesis strategy. The immobilized version of 3,4‐dihydro‐2H‐pyran, the so‐called Ellman resin, is also discussed as a useful solid support for anchoring the side chains of serine, threonine and tryptophan residues.

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