TY - JOUR
T1 - Total synthesis of (+)-1893B aimed at establishing its stereochemistry
AU - Yasui, Hiroyuki
AU - Hirai, Kunihiro
AU - Yamamoto, Shun
AU - Takao, Ken ichi
AU - Tadano, Kin ichi
PY - 2006/1/1
Y1 - 2006/1/1
N2 - The total synthesis of (+)-1893B (2) has been completed. The one-pot ring-opening/cross/ring-closing metathesis of (1S,2S,3S,4R)-2-(t-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene (4) provided (1R,6S,7S,8S)-7-hydroxymethyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene (6) after deblocking. The epoxy-ring opening of an advanced intermediate (1R,6S,7S,8S)-7-[(1S,2S)-1-methoxymethoxy-2,3-epoxypropyl]-8-methyl-9-oxabi cyclo[4.2.1]nona-2,4-diene (11a) with trimethylsilylacetylide, followed by palladium(II)-catalyzed oxidation for construction of the γ-lactone moiety in 2.
AB - The total synthesis of (+)-1893B (2) has been completed. The one-pot ring-opening/cross/ring-closing metathesis of (1S,2S,3S,4R)-2-(t-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene (4) provided (1R,6S,7S,8S)-7-hydroxymethyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene (6) after deblocking. The epoxy-ring opening of an advanced intermediate (1R,6S,7S,8S)-7-[(1S,2S)-1-methoxymethoxy-2,3-epoxypropyl]-8-methyl-9-oxabi cyclo[4.2.1]nona-2,4-diene (11a) with trimethylsilylacetylide, followed by palladium(II)-catalyzed oxidation for construction of the γ-lactone moiety in 2.
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U2 - 10.3987/COM-05-S(T)42
DO - 10.3987/COM-05-S(T)42
M3 - Article
AN - SCOPUS:33646893053
SN - 0385-5414
VL - 67
SP - 123
EP - 128
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -