Total Synthesis of Paecilomycine A

Min, Sun‐Joon

doi:10.1002/anie.200605058

Cited by 58 publications

(12 citation statements)

References 37 publications

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“…Scheme 17 features a number of other excellent examples of syntheses that display striking levels of step, redox, or atom economy. [30][31][32][33][34][35][36][37] Scheme 15 Addressing the supply problem of Tamiflu (110).…”

Section: Suggested Further Readingmentioning

confidence: 99%

The economies of synthesis

2009

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In this tutorial review the economies of synthesis are analysed from both detailed and macroscopic perspectives, using case-studies from complex molecule synthesis. Atom, step, and redox economy are more than philosophical constructs, but rather guidelines, which enable the synthetic chemist to design and execute an efficient synthesis. Students entering the field of synthesis might find this tutorial helpful for understanding the subtle differences between these economic principles and also see real-world situations where such principles are put into practice.

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Section: Suggested Further Readingmentioning

confidence: 99%

The economies of synthesis

2009

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“…The PKR has been applied to the synthesis of many natural products: (±)-pentalenene, 118 (+)-hirsutene, 82 (-)-kainic acid, 119 (+)-brefeldin A, 120 (+)-epoxydictymene, 121 (±)-asteriscanolide, (±)-oc-and ß-cedrene, 125,111 , x · ·,,· 126 122 Japanese Hop Ether, 127 123,124 (-)" alstonerine 1^' "', (-)-incarvilline, lzo paecilomycine,' z/ and (+)-(Xskytanthine. 8 The Scheme on page 169 shows the PKR disconnections used to assemble these natural products.…”

Section: Applications In Total Synthesismentioning

confidence: 99%

Five‐Membered Carbocycles

2010

Name Reactions for Carbocyclic Ring Formations

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“…( 3 ) To date, we have synthesized and evaluated a range of these neurologically active small molecules, including tricycloillicinone,( 4 ) merrilactone A,( 5 ) scabronine G methyl ester,( 6 ) NGA0187,( 7 ) jiadifenin,( 8 ) 11- O- debenzoyltashironin,( 9 ) garsubellin A,( 10 ) and paecilomycine A. ( 11 ) Our involvement in this field also led us to pursue the total synthesis of the structurally complex small molecule neurotrophins, spirotenuipesines A and B. ( 12 )…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Spirotenuipesines A and B

Dai

Krauss

2008

J. Org. Chem.

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Spirotenuipesines A and B, isolated from the entomopathogenic fungus Paecilomyces tenuipes by Oshima and co-workers, have been synthesized. The synthesis features the highly stereoselective construction of two vicinal all-carbon quaternary centers (C5 and C6) via an intramolecular cyclopropanation/radical initiated fragmentation sequence and a diastereoselective intermolecular Diels−Alder reaction between α-methylenelactone dienophile 20 and synergistic diene 6a. Installation of the C9 tertiary alcohol occurred via nucleophilic methylation. An RCM reaction to produce a tetrasubstituted double bond in the presence of free allylic alcohol and homoallylic oxygenated functional group is also described. This route shortened the synthesis of 11 from 9 steps to 3 steps. We have further developed a strategy to gain access to optically active spirotenuipesines A and B through the synthesis of enantioenriched 10 from commercially available R-(−)-epichlorohydrin.

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Total Synthesis of Paecilomycine A

Cited by 58 publications

References 37 publications

The economies of synthesis

The economies of synthesis

Five‐Membered Carbocycles

Total Synthesis of Spirotenuipesines A and B

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