TY - JOUR
T1 - Synthesis of the 5-thiorotenoid system from thiochroman-3-one
AU - Gabbutt, Christopher D.
AU - Hepworth, John D.
AU - Heron, B. Mark
PY - 1992/12/1
Y1 - 1992/12/1
N2 - Base-induced cyclisation of the diketones 10 (X = H or F), prepared in a two-step sequence from thiochroman-3-one, affords 6H,12H-[1]benzothiopyrano[3,4- b][1]benzopyran-12-ones 11. Reduction with diisobutylaluminium hydride affords a separable mixture of the cis- and trans-5-thiorotenoids. Dieckmann cyclisation of ethyl 2-(ethoxycarbonylmethylthio)phenylethanoate affords a mixture of 4-ethoxycarbonyl- and 2-ethoxycarbonyl-thiochroman-3-ones. Attempts to prepare a thiorotenoid by condensation of these β-keto esters with 4-methoxyphenol resulted in formation of the novel bis[1]benzothiopyrano[3,2-b:4′, 3′-e]pyran ring system.
AB - Base-induced cyclisation of the diketones 10 (X = H or F), prepared in a two-step sequence from thiochroman-3-one, affords 6H,12H-[1]benzothiopyrano[3,4- b][1]benzopyran-12-ones 11. Reduction with diisobutylaluminium hydride affords a separable mixture of the cis- and trans-5-thiorotenoids. Dieckmann cyclisation of ethyl 2-(ethoxycarbonylmethylthio)phenylethanoate affords a mixture of 4-ethoxycarbonyl- and 2-ethoxycarbonyl-thiochroman-3-ones. Attempts to prepare a thiorotenoid by condensation of these β-keto esters with 4-methoxyphenol resulted in formation of the novel bis[1]benzothiopyrano[3,2-b:4′, 3′-e]pyran ring system.
UR - http://www.scopus.com/inward/record.url?scp=37049073049&partnerID=8YFLogxK
U2 - 10.1039/P19920003015
DO - 10.1039/P19920003015
M3 - Article
AN - SCOPUS:37049073049
SP - 3015
EP - 3018
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 22
ER -