TY - JOUR
T1 - Stereocontrolled syntheses of (-)-goniofufurone and (-)-8-epi-goniofufurone
AU - Shing, Tony K.M.
AU - Tsui, Hon Chung
AU - Zhou, Zhao Hui
PY - 1992
Y1 - 1992
N2 - The absolute configurations of natural goniofufurone and 8-epi-goniofufurone are shown to be 2 and 4 respectively by unambiguous syntheses of their enantiomers 1 and 3 from d-glycero-d-gulo-heptono-γ-lactone 7 involving an intramolecular Michael reaction as the key step. The diol 6, readily availble from d-glycero-d-gulo-heptono-γ-lactone, has been converted by six sequential reactions (acetylation, hydrolysis, deacetylation, glycol cleavage, Wittig reaction, and hydrolysis) into the γ-lactone 5 which underwent an intramolecular Michael reaction to yield (-)-goniofufurone 1. Likewise reactions of the monoacetate 12 gave (-)-8-epi-goniofufurone 3.
AB - The absolute configurations of natural goniofufurone and 8-epi-goniofufurone are shown to be 2 and 4 respectively by unambiguous syntheses of their enantiomers 1 and 3 from d-glycero-d-gulo-heptono-γ-lactone 7 involving an intramolecular Michael reaction as the key step. The diol 6, readily availble from d-glycero-d-gulo-heptono-γ-lactone, has been converted by six sequential reactions (acetylation, hydrolysis, deacetylation, glycol cleavage, Wittig reaction, and hydrolysis) into the γ-lactone 5 which underwent an intramolecular Michael reaction to yield (-)-goniofufurone 1. Likewise reactions of the monoacetate 12 gave (-)-8-epi-goniofufurone 3.
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U2 - 10.1016/S0040-4020(01)89441-2
DO - 10.1016/S0040-4020(01)89441-2
M3 - Article
AN - SCOPUS:0026758501
SN - 0040-4020
VL - 48
SP - 8659
EP - 8666
JO - Tetrahedron
JF - Tetrahedron
IS - 40
ER -