Literature DB >> 12659567

Enantioselective synthesis of alpha-methyl-D-cysteine and lanthionine building blocks via alpha-methyl-D-serine-beta-lactone.

Nicole D Smith1, Murray Goodman.   

Abstract

[reaction: see text] We report here the enantioselective synthesis of Boc-alpha-methyl-d-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-alpha-methyl-d-serine-beta-lactone.

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Year:  2003        PMID： 12659567     DOI： 10.1021/ol034025p

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


  6 in total

1.  Synthesis of Chiral Nonracemic Tertiary α-Thio and α-Sulfonyl Acetic Esters via S(N)2 reactions of Tertiary Mesylates.

Authors:  Jimmie D Weaver; David K Morris; Jon A Tunge
Journal:  Synlett       Date:  2010-02-01       Impact factor: 2.454

2.  Total syntheses of the histone deacetylase inhibitors largazole and 2-epi-largazole: application of N-heterocyclic carbene mediated acylations in complex molecule synthesis.

Authors:  Bo Wang; Po-Hsien Huang; Ching-Shih Chen; Craig J Forsyth
Journal:  J Org Chem       Date:  2011-01-18       Impact factor: 4.354

3.  tert-Butyl N-[(S)-3-isobutyl-2-oxooxetan-3-yl]carbamate.

Authors:  Lesław Sieroń; Adam Kudaj; Aleksandra Olma; Janina Karolak-Wojciechowska
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-06

4.  tert-Butyl N-[(S)-3-isopropyl-2-oxo-oxetan-3-yl]carbamate.

Authors:  Lesław Sieroń; Adam Kudaj; Aleksandra Olma; Janina Karolak-Wojciechowska
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-06

5.  Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor.

Authors:  Albert Bowers; Nathan West; Jack Taunton; Stuart L Schreiber; James E Bradner; Robert M Williams
Journal:  J Am Chem Soc       Date:  2008-07-19       Impact factor: 15.419

6.  The role of phosphate in a multistep enzymatic reaction: reactions of the substrate and intermediate in pieces.

Authors:  Svetlana A Kholodar; C Leigh Allen; Andrew M Gulick; Andrew S Murkin
Journal:  J Am Chem Soc       Date:  2015-02-10       Impact factor: 15.419
  6 in total

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