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Literature DB >> 19725523

Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

Partha Ghosh¹, Yue Zhang, Thomas J Emge, Lawrence J Williams.

Abstract

A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2009 PMID： 19725523 PMCID： PMC3044927 DOI： 10.1021/ol901755a

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

9 in total

1. [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.

Authors: Zhi-Hui Peng; K A Woerpel
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

2. An abiotic strategy for the enantioselective synthesis of erythromycin B.

Authors: Paul J Hergenrother; Anne Hodgson; Andrew S Judd; Wen-Cherng Lee; Stephen F Martin
Journal: Angew Chem Int Ed Engl Date: 2003-07-21 Impact factor: 15.336

Review 3. Macrolactonizations in the total synthesis of natural products.

Authors: A Parenty; X Moreau; J-M Campagne
Journal: Chem Rev Date: 2006-03 Impact factor: 60.622

4. Spirodiepoxide reaction with cuprates.

Authors: Partha Ghosh; Stephen D Lotesta; Lawrence J Williams
Journal: J Am Chem Soc Date: 2007-02-09 Impact factor: 15.419

5. Spirodiepoxides: heterocycle synthesis and mechanistic insight.

Authors: Stephen D Lotesta; Sezgin Kiren; Ronald R Sauers; Lawrence J Williams
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

6. Total synthesis of erythronolide A by Mg(II)-mediated cycloadditions of nitrile oxides.

Authors: Dieter Muri; Nina Lohse-Fraefel; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2005-06-27 Impact factor: 15.336

7. Spirodiepoxides in total synthesis: epoxomicin.

Authors: Sreenivas Katukojvala; Kristin N Barlett; Stephen D Lotesta; Lawrence J Williams
Journal: J Am Chem Soc Date: 2004-12-01 Impact factor: 15.419

8. A formal synthesis of psymberin.

Authors: Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal: Org Lett Date: 2007-02-24 Impact factor: 6.005

9. A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4.

Authors: Stephen D Lotesta; Yongquan Hou; Lawrence J Williams
Journal: Org Lett Date: 2007-02-08 Impact factor: 6.005

9 in total

11 in total

Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

1. [3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.

2. An abiotic strategy for the enantioselective synthesis of erythromycin B.

Review 3. Macrolactonizations in the total synthesis of natural products.

4. Spirodiepoxide reaction with cuprates.

5. Spirodiepoxides: heterocycle synthesis and mechanistic insight.

6. Total synthesis of erythronolide A by Mg(II)-mediated cycloadditions of nitrile oxides.

7. Spirodiepoxides in total synthesis: epoxomicin.

8. A formal synthesis of psymberin.

9. A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4.

1. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

2. Desmethyl Macrolides: Synthesis and Evaluation of 4,8-Didesmethyl Telithromycin.

3. Spirodiepoxide-based cascades: direct access to diverse motifs.

4. Modular functionalization of allenes to aminated stereotriads.

5. Desmethyl Macrolides: Synthesis and Evaluation of 4,10-Didesmethyl Telithromycin.

6. Direct entry to erythronolides via a cyclic bis[allene].

7. Spirodiepoxide strategy to the C ring of pectenotoxin 4: synthesis of the C1-C19 sector.

8. Spirodiepoxides: synthesis of epoxomicinoids.

9. The chemistry of bisallenes.

10. Toward an integrated route to the vernonia allenes and related sesquiterpenoids.