Literature DB >> 16435851

Synthetic studies on amphidinolide B1.

Amit K Mandal1, John S Schneekloth, Kouji Kuramochi, Craig M Crews.   

Abstract

[structure: see text]. The syntheses of three fragments, 2, 3, and 4, of amphidinolide B1 have been accomplished. The 1,3-isomerization of allylic alcohol 10 was accomplished via rhenium oxo catalysis and has been applied successfully in the synthesis. (-)-MIB-catalyzed asymmetric vinylzinc addition to aldehyde 31 and the regio- and stereoselective epoxidation of unsymmetrical divinyl methanol 32 were key steps.

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Year:  2006        PMID： 16435851      PMCID： PMC2507747          DOI： 10.1021/ol052620g

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


  8 in total

1.  Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors:  Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

2.  Cytotoxic macrolides from a cultured marine dinoflagellate of the genus Amphidinium.

Authors:  J Kobayashi; M Ishibashi; H Nakamura; Y Ohizumi; T Yamasu; Y Hirata; T Sasaki; T Ohta; S Nozoe
Journal:  J Nat Prod       Date:  1989 Sep-Oct       Impact factor: 4.050

Review 3.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

Review 4.  Chemistry of potent anti-cancer compounds, amphidinolides.

Authors:  T K Chakraborty; S Das
Journal:  Curr Med Chem Anticancer Agents       Date:  2001-08

5.  Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.

Authors:  Amit K Mandal; John S Schneekloth; Craig M Crews
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

6.  A general, highly enantioselective method for the synthesis of D and L alpha-amino acids and allylic amines.

Authors:  Young K Chen; Alice E Lurain; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2002-10-16       Impact factor: 15.419

7.  Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes.

Authors:  H C Brown; K S Bhat
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

Review 8.  Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

Authors:  Jun'ichi Kobayashi; Masashi Tsuda
Journal:  Nat Prod Rep       Date:  2004-01-07       Impact factor: 13.423
  8 in total
  14 in total

1.  Synthesis of the C3-C18 fragment of amphidinolides G and H.

Authors:  Andreas F Petri; John S Schneekloth; Amit K Mandal; Craig M Crews
Journal:  Org Lett       Date:  2007-07-07       Impact factor: 6.005

2.  Total synthesis of cytotoxic macrolide amphidinolide B1 and the proposed structure of amphidinolide B2.

Authors:  Liang Lu; Wei Zhang; Rich G Carter
Journal:  J Am Chem Soc       Date:  2008-05-20       Impact factor: 15.419

3.  Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors:  Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal:  J Org Chem       Date:  2013-02-13       Impact factor: 4.354

4.  Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.

Authors:  Cyril Bucher; Richard M Deans; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2015-09-29       Impact factor: 15.419

5.  Synthesis of a C1-C23 fragment of the archazolids and evidence for V-ATPase but not COX inhibitory activity.

Authors:  Gregory W O'Neil; Alexander M Craig; John R Williams; Jeffrey C Young; P Clint Spiegel
Journal:  Synlett       Date:  2017-02-08       Impact factor: 2.454

6.  Enantioselective total synthesis of amphidinolide F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-05       Impact factor: 15.336

7.  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

8.  Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.

Authors:  P C Ravikumar; Lihua Yao; Fraser F Fleming
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

9.  Application of tandem ring-closing enyne metathesis: formal total synthesis of (-)-cochleamycin A.

Authors:  Sumit Mukherjee; Daesung Lee
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

10.  Direct Conversion of Aldehydes and Ketones to Allylic Halides by a NbX(5-)[3,3] Rearrangement.

Authors:  Fraser F Fleming; P C Ravikumar; Lihua Yao
Journal:  Synlett       Date:  2009       Impact factor: 2.454
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