The first total synthesis of (-)-solanapyrone E based on domino Michael strategy

Authors
Hagiwara, H Kobayashi, K Miya, S Hoshi, T Suzuki, T Ando, M
Citation
H. Hagiwara et al., The first total synthesis of (-)-solanapyrone E based on domino Michael strategy, ORG LETT, 3(2), 2001, pp. 251-254
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
2
Year of publication
2001
Pages
251 - 254
Database
ISI
SICI code
1523-7060(20010125)3:2<251:TFTSO(>2.0.ZU;2-9
Abstract
[GRAPHICS] A phytotoxin, solanapyrone E, has been synthesized from the decalone prepar ed by the domino Michael reaction of the kinetic enolate of optically pure acetylcyclohexene with methyl crotonate, After several transformations on t he decalone ring, condensation of a methyl acetoacetate equivalent installe d a pyrone moiety and introduction of a hydroxymethyl unit into the pyrone ring furnished solanapyrone E.