Literature DB >> 18205377

Synthesis of the C(26)-C(42) and C(43)-C(67) pyran-containing fragments of amphidinol 3 via a common pyran intermediate.

Jacqueline D Hicks1, William R Roush.   

Abstract

The pyran-containing fragments 1 and 2 of AM3 have been synthesized from the common pyran intermediate 3. Careful orchestration of the alcohol protecting groups was necessary to facilitate deprotection of alcohol functionality in the presence of the chemically sensitive polyene chain.

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Year:  2008        PMID： 18205377     DOI： 10.1021/ol703042q

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


  7 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

2.  Total synthesis of (-)-CP2-disorazole C1.

Authors:  Chad D Hopkins; John C Schmitz; Edward Chu; Peter Wipf
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

3.  Synthesis of the bis-tetrahydropyran core of amphidinol 3.

Authors:  Michael T Crimmins; Timothy J Martin; Theodore A Martinot
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

4.  Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences.

Authors:  Ming Chen; Masaki Handa; William R Roush
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

5.  Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2013-06-12       Impact factor: 15.419

6.  Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment.

Authors:  Takashi Tomioka; Yusuke Takahashi; Toshihide Maejima; Yuki Yabe; Hiroki Iwata; Mark T Hamann
Journal:  Tetrahedron Lett       Date:  2013-11-01       Impact factor: 2.415

7.  A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

Authors:  Aleksandr Grisin; P Andrew Evans
Journal:  Chem Sci       Date:  2015-08-06       Impact factor: 9.825
  7 in total

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