Literature DB >> 15469369

Synthesis of the C11-C29 fragment of amphidinolide F.

J Brad Shotwell1, William R Roush.   

Abstract

[reaction: see text] An efficient synthesis of the C(11)-C(29) fragment 31 of amphidinolide F has been accomplished via a diastereoselective [3 + 2]-annulation reaction of allylsilane 5 and ethyl glyoxylate to prepare the key tetrahydrofuran 15 and a highly stereoselective methyl ketone aldol reaction to generate the C(11)-C(16) segment.

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Year:  2004        PMID： 15469369     DOI： 10.1021/ol048381z

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


  16 in total

1.  A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction.

Authors:  Mahesh P Paudyal; Nigam P Rath; Christopher D Spilling
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  Enantioselective syntheses of syn- and anti-β-hydroxyallylsilanes via allene hydroboration-aldehyde allylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2011-03-16       Impact factor: 6.005

3.  Efficient protiodesilylation of unactivated C(sp3)-SiMe2Ph bonds using tetrabutylammonium fluoride.

Authors:  Cheryl L Heitzman; William T Lambert; Eric Mertz; J Brad Shotwell; Jennifer M Tinsley; Porino Va; William R Roush
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

4.  Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Authors:  Sheila Namirembe; Lu Yan; James P Morken
Journal:  Org Lett       Date:  2020-11-12       Impact factor: 6.005

5.  Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C.

Authors:  Robert H Bates; J Brad Shotwell; William R Roush
Journal:  Org Lett       Date:  2008-09-11       Impact factor: 6.005

6.  Studies for the total synthesis of amphidinolide P.

Authors:  David R Williams; Brian J Myers; Liang Mi; Randall J Binder
Journal:  J Org Chem       Date:  2013-04-26       Impact factor: 4.354

7.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

8.  Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  Org Biomol Chem       Date:  2009-09-16       Impact factor: 3.876

9.  Diastereoselective synthesis of tetrahydrofurans via mead reductive cyclization of keto-beta-lactones derived from the tandem Mukaiyama aldol lactonization (TMAL) process.

Authors:  T Andrew Mitchell; Daniel Romo
Journal:  J Org Chem       Date:  2007-11-01       Impact factor: 4.354

10.  Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2010-10-28       Impact factor: 6.005
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