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

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

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

2011 ◽  
Vol 123 (37) ◽  
pp. 8898-8903 ◽  
Author(s):  
Stefan Benson ◽  
Marie-Pierre Collin ◽  
Alexander Arlt ◽  
Barbara Gabor ◽  
Richard Goddard ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Second Generation

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 new strategy for C20 gibberellin synthesis: total synthesis of (.+-.)-gibberellin A38 methyl ester

1983 ◽  
Vol 48 (13) ◽  
pp. 2298-2300 ◽  
Author(s):  
Luciano Lombardo ◽  
Lewis N. Mander
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
New Strategy

Stereoselective total synthesis of preclavulone-A methyl ester and its diastereomer

2004 ◽  
Vol 45 (9) ◽  
pp. 1941-1944 ◽  
Author(s):  
Hisanaka Ito ◽  
Masami Konishi ◽  
Kazuo Iguchi
Keyword(s):  
Methyl Ester ◽  
Total Synthesis

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

ChemInform Abstract: Stereocontrolled Total Synthesis of (.+-.)-Pentalenolactone P Methyl Ester.

ChemInform ◽  
2010 ◽  
Vol 23 (12) ◽  
pp. no-no
Author(s):  
H.-J. KANG ◽  
C. S. RA ◽  
L. A. PAQUETTE
Keyword(s):  
Methyl Ester ◽  
Total Synthesis

scholarly journals Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene: a general intramolecular Diels–Alder approach to tricyclic sesquiterpenes

1985 ◽  
Vol 63 (4) ◽  
pp. 993-995 ◽  
Author(s):  
Kazimierz Antczak ◽  
John F. Kingston ◽  
Alex G. Fallis
Keyword(s):  
Double Bond ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Ring System ◽  
Diels Alder ◽  
Exocyclic Double Bond ◽  
Total Syntheses ◽  
Methyl Group ◽  
Secondary Hydroxyl ◽  
Selective Hydrogenolysis

Stereoselective total synthesis of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl)-2-pentenoate 11 affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (12) which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function (Ph3P/CCl4/CH3CN; H2/Pd/C), reduction of the methyl ester (LiAlH4), and introduction of the exocyclic double bond (acetate pyrolysis, 550 °C) completes the synthesis of (±)-sinularene in 14 steps from cyclopentadiene. A parallel series of reactions employing the isopropyl epimer of 12 affords (±)-5-epi-sinularene.

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