A short, vinyl radical cyclisation approach to (±))-2-pupukeanone

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 2003-2004

  Srikrishna, A ^a   Vijaykumar, D ^a   Sharma, G V R ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 PUPUKEANONE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0031575736     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00210-4     Document Type: Article

References (9)

1. 1. Burreson, B.J.; Scheuer, P.J.; Finer, J.; Clardy, J. J. Am. Chem. Soc., 1975, 97, 4763.
2. 2. (a) Corey, E.J.; Ishiguro, M. Tetrahedron Lett., 1979, 2745.
3. (b) Frater, G.; Wenger, J. Helv. Chim. Acta, 1984, 67, 1702.
4. (c) Subba Rao, G.S.R.; Kaliappan, K. Tetrahedron Lett., 1997, 38, 0000.
5. 3. Chang, N.-C.; Chang, C.-K. J. Org. Chem., 1996, 61, 4967.
6. 2c have achieved the total synthesis of 2-pupukeanone starting from dihydroanisole-ketene Diels-Alder adduct, using two acid mediated rearrangements and an allyl radical cyclisation reaction as key steps.
7. 5. Nunez, M.T.; Martin, V.S. J. Og. Chem., 1990, 55, 1928.
8. +).
9. 7. To establish the generality, the sequence was also carried out successfully using methyl acrylate and methyl vinyl ketones as dienophiles.