TY - JOUR
T1 - Enantioselective total synthesis and stereochemical revision of communiols E and F
AU - Enomoto, Masaru
AU - Kuwahara, Shigefumi
PY - 2006/8/1
Y1 - 2006/8/1
N2 - The enantioselective total synthesis of candidate structures for communiols E and F, novel bicyclic polyketides of fungal origin, was accomplished using a Lewis acid-mediated ring closure reaction of an allylsilane intermediate as the key step. Comparison of the spectral data of the synthetic materials with those of natural communiols E and F, coupled with biosynthetic considerations, led to the conclusion that the stereochemistry of communiols E and F should be (2S,5S,TR, 8S,11R)- and (5S,7R,8S,11R)-forms, respectively.
AB - The enantioselective total synthesis of candidate structures for communiols E and F, novel bicyclic polyketides of fungal origin, was accomplished using a Lewis acid-mediated ring closure reaction of an allylsilane intermediate as the key step. Comparison of the spectral data of the synthetic materials with those of natural communiols E and F, coupled with biosynthetic considerations, led to the conclusion that the stereochemistry of communiols E and F should be (2S,5S,TR, 8S,11R)- and (5S,7R,8S,11R)-forms, respectively.
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U2 - 10.1021/jo0608927
DO - 10.1021/jo0608927
M3 - Article
C2 - 16872223
AN - SCOPUS:33746930284
SN - 0022-3263
VL - 71
SP - 6287
EP - 6290
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -