A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester

2012 ◽  
Vol 51 (11) ◽  
pp. 2749-2753 ◽  
Author(s):  
Ian Paterson ◽  
Philip Maltas ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Edward A. Anderson
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Second Generation ◽  
Spirastrellolide A

Total synthesis of (+)-spirastrellolide A methyl ester: Challenges and discoveries

2013 ◽  
Vol 85 (6) ◽  
pp. 1133-1147 ◽  
Author(s):  
Ian Paterson ◽  
Philip Maltas ◽  
Edward A. Anderson
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Second Generation ◽  
Protecting Groups ◽  
Ring Systems ◽  
Linker Region ◽  
Anticancer Properties ◽  
Spirastrellolide A

This review focuses on recent synthetic efforts by our group towards spirastrellolide A methyl ester, a complex marine macrolide containing two spiroacetal ring systems that shows promising anticancer properties. The evolution of a flexible, modular strategy leading to the first total synthesis of (+)-spirastrellolide A methyl ester, and the associated challenges overcome, are highlighted, particularly in dealing with the initial structural ambiguities. This work enabled the development of an improved second-generation synthesis, which revealed a critical dependence of the key macrolactonization step on the nature of the protecting groups in the linker region between the spiroacetal motifs.

A Second-Generation Total Synthesis of Spirastrellolide A Methyl Ester

2012 ◽  
Vol 124 (11) ◽  
pp. 2803-2807 ◽  
Author(s):  
Ian Paterson ◽  
Philip Maltas ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Edward A. Anderson
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Second Generation ◽  
Spirastrellolide A

A Total Synthesis of Spirastrellolide A Methyl Ester

2013 ◽  
Vol 19 (11) ◽  
pp. 3596-3608 ◽  
Author(s):  
Alexander Arlt ◽  
Stefan Benson ◽  
Saskia Schulthoff ◽  
Barbara Gabor ◽  
Alois Fürstner
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments

2012 ◽  
Vol 10 (30) ◽  
pp. 5861 ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Philip Maltas ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

The stereocontrolled total synthesis of spirastrellolide A methyl ester. Fragment coupling studies and completion of the synthesis

2012 ◽  
Vol 10 (30) ◽  
pp. 5873 ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Philip Maltas
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

Total Synthesis of Spirastrellolide A Methyl Ester—Part 2: Subunit Union and Completion of the Synthesis

2008 ◽  
Vol 120 (16) ◽  
pp. 3063-3067 ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Julien Genovino ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

Total Synthesis of Spirastrellolide A Methyl Ester—Part 1: Synthesis of an Advanced C17–C40 Bis-spiroacetal Subunit

2008 ◽  
Vol 120 (16) ◽  
pp. 3058-3062 ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Julien Genovino ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

Second-Generation Total Synthesis of Spirastrellolide F Methyl Ester: The Alkyne Route

2011 ◽  
Vol 50 (37) ◽  
pp. 8739-8744 ◽  
Author(s):  
Stefan Benson ◽  
Marie-Pierre Collin ◽  
Alexander Arlt ◽  
Barbara Gabor ◽  
Richard Goddard ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Second Generation

ChemInform Abstract: Total Synthesis of Spirastrellolide A Methyl Ester. Part 1. Synthesis of an Advanced C17-C40 Bis-spiroacetal Subunit.

ChemInform ◽  
2008 ◽  
Vol 39 (34) ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Julien Genovino ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A

Total Synthesis of Spirastrellolide A Methyl Ester—Part 2: Subunit Union and Completion of the Synthesis

2008 ◽  
Vol 47 (16) ◽  
pp. 3021-3025 ◽  
Author(s):  
Ian Paterson ◽  
Edward A. Anderson ◽  
Stephen M. Dalby ◽  
Jong Ho Lim ◽  
Julien Genovino ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Spirastrellolide A
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