Total synthesis of (+)-aspicilin from D-mannitol

Synlett

Volumn , Issue 17, 2009, Pages 2828-2830

  Yadav, J S ^a   Rao, T Srinivasa ^a   Ravindar, K ^a   Reddy, B V Subba ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

(+) aspicilin; D mannitol; Kinetic resolution; Masamune Roush olefination; Ring closing metathesis; Swern

Indexed keywords

ALDEHYDE DERIVATIVE; ASPICILIN; ESTER; ESTER DERIVATIVE; MACROLIDE; MANNITOL; OLEFINIC ALDEHYDE; OLEFINIC PHOSPHONATE ESTER; TRIENTINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HYDROLYSIS KINETICS; MASAMUNE ROUSH OLIFENATION; OLEFINATION; RING CLOSING METATHESIS; SWERN OXIDATION; SYNTHESIS;

EID: 70449433312     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217974     Document Type: Article

References (13)

1. Hesse O, J. Prakt. Chem. 1900 62 430, Hesse O, J.
2. Huneck S, Schreiber K, Steglich W, Tetrahedron 1973 29 3687
3. Quinkert G, Heim N, Bats J W., Oshkinat H, Kessler H, Angew.
4. Banwell M G., Mcrae K, J.
5. Chakraborty T K., Ghosh S, Rao M H. V. R., Kunwar A C., Cho H, Ghosh A K., Tetrahedron
6. Garegg P G., Samuclson B, Synthesis 1979 813
7. Tolstikov G A., Miftakhov M S., Vostrikov N S., Komissarova N G., Adler M E., Kuznetsov O M., Zh. Org. Khim. 1988 24 224; Chem. Abstr. 1989, 110, 7162
8. Tolstikov G A., Miiftakhov M S., Alder M E., Komissarova N G., Kuznetsov O M., Vostrikov N S., Synthesis 1989 940
9. Tokunaga M, Larrow J F., Kakiuchi F, Jacobsen [nl]E N., Science 1997 277 936, Schaus S E., Brandes B D., Larrow J F., Tokunaga M, Hansen K B., Gould A E., Furrow M E., Jacobsen E N., J. Am. Chem. Soc. 2002 124 1307 The epoxide 12 was analysed by chiral HPLC using Chiralcel
10. Banwell M G., McRae K J., Org. Lett. 2000 2 3583
11. Blanchette M A., Choy W, Davis J T., Essenfeld A P., Masamune S, Roush W R., Sakai T, Tetrahedron
12. Trnka T M., Grubbs R H., Acc. Chem. Res. 2001 34 18
13. Nishioka T, Iwabuchi Y, Irie H, Hatakeyama S, Tetrahedron Lett. 1998 39 5597