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Literature DB >> 18489095

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

Abstract

The first enantioselective total syntheses of cytotoxic macrolide amphidinolide B1 and the proposed structure for amphidinolide B2 have been accomplished. Key features of the syntheses include a diastereoselective aldol condensation, a spontaneous Wadsworth-Emmons macrocyclization and a directed epoxidation/elimination sequence.

Entities: Chemical

Mesh：

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Year: 2008 PMID： 18489095 PMCID： PMC2435505 DOI： 10.1021/ja803012n

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

8 in total

1. Biosynthetic study of amphidinolide B.

Authors: M Tsuda; T Kubota; Y Sakuma; J Kobayashi
Journal: Chem Pharm Bull (Tokyo) Date: 2001-10 Impact factor: 1.645

2. 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

3. Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.

Authors: Xiao-Ti Zhou; Liang Lu; Daniel P Furkert; Charles E Wells; Rich G Carter
Journal: Angew Chem Int Ed Engl Date: 2006-11-20 Impact factor: 15.336

4. Synthetic studies on amphidinolide B1.

Authors: Amit K Mandal; John S Schneekloth; Kouji Kuramochi; Craig M Crews
Journal: Org Lett Date: 2006-02-02 Impact factor: 6.005

5. Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

Authors: Wei Zhang; Rich G Carter
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

6. 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

8. Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.

Authors: Jing Li; Alexander Preinfalk; Nuno Maulide
Journal: Angew Chem Int Ed Engl Date: 2019-03-27 Impact factor: 15.336

8 in total

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

1. Biosynthetic study of amphidinolide B.

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

3. Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.

4. Synthetic studies on amphidinolide B1.

5. Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

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

7. Amphidinolide B: asymmetric synthesis of a C7-C20 synthon.

8. One-pot asymmetric synthesis of acyclic chiral epoxy alcohols via tandem vinylation-epoxidation with dioxygen.

Review 1. Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

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

3. Enantioselective total synthesis of amphidinolide F.

4. Polyol synthesis with beta-oxyanionic alkyllithium reagents: syntheses of aculeatins A, B, and D.

5. Studies for the total synthesis of amphidinolide P.

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

7. Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

8. Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.