Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Literature DB >> 15049660

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

Wei Zhang¹, Rich G Carter, Alexandre F T Yokochi.

Abstract

The efficient synthesis of the C(19)-C(26) subunit of amphidinolide B(1) and B(2) has been completed using a boron-mediated aldol reaction. The synthesis of the C(19)-C(26) subunit of amphidinolide B(3) has also been accomplished through an unexpected anti aldol reaction using a titanium-mediated process. In addition, the first reported examples of a stereochemical discrepancy between the Evans' boron-mediated oxazolidinone and the Crimmins' titanium-mediated oxazolidinethione aldol reactions are disclosed. A working hypothesis is put forth to explain the results.

Entities: Chemical

Mesh：

Substances：

Year: 2004 PMID： 15049660 PMCID： PMC2430272 DOI： 10.1021/jo035829l

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

17 in total

1. Resurrecting the Cornforth model for carbonyl addition: studies on the origin of 1,2-asymmetric induction in enolate additions to heteroatom-substituted aldehydes.

Authors: David A Evans; Sarah J Siska; Victor J Cee
Journal: Angew Chem Int Ed Engl Date: 2003-04-17 Impact factor: 15.336

2. Total synthesis of amphidinolide T4.

Authors: Alois Fürstner; Christophe Aïssa; Ricardo Riveiros; Jacques Ragot
Journal: Angew Chem Int Ed Engl Date: 2002-12-16 Impact factor: 15.336

3. Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.

Authors: Robert E Maleczka; Lamont R Terrell; Feng Geng; Joseph S Ward
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

4. Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Authors: M T Crimmins; B W King; E A Tabet; K Chaudhary
Journal: J Org Chem Date: 2001-02-09 Impact factor: 4.354

5. Ruthenium-catalyzed alkene-alkyne coupling: synthesis of the proposed structure of amphidinolide A.

Authors: Barry M Trost; John D Chisholm; Stephen T Wrobleski; Michael Jung
Journal: J Am Chem Soc Date: 2002-10-23 Impact factor: 15.419

6. An efficient, general asymmetric synthesis of carbocyclic nucleosides: application of an asymmetric aldol/ring-closing metathesis strategy.

Authors: M T Crimmins; B W King; W J Zuercher; A L Choy
Journal: J Org Chem Date: 2000-12-15 Impact factor: 4.354

7. Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones.

Authors: David A Evans; C Wade Downey; Jared T Shaw; Jason S Tedrow
Journal: Org Lett Date: 2002-04-04 Impact factor: 6.005

8. Total synthesis of epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D.

Authors: J D White; R G Carter; K F Sundermann; M Wartmann
Journal: J Am Chem Soc Date: 2001-06-13 Impact factor: 15.419

9. Enantioselective total synthesis of (+)-amphidinolide t1.

Authors: Arun K Ghosh; Chunfeng Liu
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

10. Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between L-erythrulose derivatives and chiral aldehydes. The Felkin-Anh versus Cornforth dichotomy.

Authors: J Alberto Marco; Miguel Carda; Santiago Díaz-Oltra; Juan Murga; Eva Falomir; Harald Roeper
Journal: J Org Chem Date: 2003-10-31 Impact factor: 4.354

11 in total

1. 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

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. 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

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. Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Authors: Ashutosh Pal; Zhenghong Peng; Paul T Schuber; Basvoju A Bhanu Prasad; William G Bornmann
Journal: Tetrahedron Lett Date: 2013-10-09 Impact factor: 2.415

7. Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

Authors: Barry M Trost; Julien P N Papillon; Thomas Nussbaumer
Journal: J Am Chem Soc Date: 2005-12-21 Impact factor: 15.419

8. Highly stereoselective and scalable anti-aldol reactions using N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and origins of stereoselectivities.

Authors: Hua Yang; Subham Mahapatra; Paul Ha-Yeon Cheong; Rich G Carter
Journal: J Org Chem Date: 2010-11-05 Impact factor: 4.354

9. 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

10. (R)-2-Phen-oxy-1-(4-phenyl-2-sulfan-ylidene-1,3-oxazolidin-3-yl)ethanone.

Authors: Ignez Caracelli; Daniel C S Coelho; Paulo R Olivato; Thiago C Correra; Alessandro Rodrigues; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-09-30